Novel halogen-substituted compounds

ABSTRACT

The invention relates inter alia to halogen-substituted compounds of the general formula (II) 
     
       
         
         
             
             
         
       
     
     in which the radicals A 1 -A 4 , T, n, W, Q, R 1  and Z 1 -Z 3  have the meanings given in the description. Also described are processes for preparing the compounds of the formula (II). The compounds according to the invention are particularly suitable for controlling insects, arachnids and nematodes in agriculture and ectoparasites in veterinary medicine.

The present application relates to novel halogen-substituted compounds,to processes for their preparation and to their use for controllinganimal pests, in particular arthropods and especially insects, arachnidsand nematodes.

It is known that certain halogen-substituted compounds have herbicidalaction (cf. J. Org. Chem. 1997, 62(17), 5908-5919, J. Heterocycl. Chem.1998, 35(6), 1493-1499, WO 2004/035545, WO 2004/106324, US 2006/069132,WO 2008/029084).

Furthermore, it is known that certain halogen-substituted compounds areinsecticidally active (EP1911751, WO2012-069366, WO2012-080376 &WO2012-107434).

In addition, it is known that certain halogen-substituted compounds haveFAAH-inhibitory activities (WO 2009/151991).

Modern crop protection compositions have to meet many demands, forexample in relation to efficacy, persistence and spectrum of theiraction and possible use. Questions of toxicity, the combinability withother active compounds or formulation auxiliaries play a role, as wellas the question of the expense that the synthesis of an active compoundrequires. Furthermore, resistances may occur. For all these reasons, thesearch for novel crop protection agents can never be considered ashaving been concluded, and there is a constant need for novel compoundshaving properties which, compared to the known compounds, are improvedat least in respect of individual aspects.

It was an object of the present invention to provide compounds whichwiden the spectrum of the pesticides under various aspects and/orimprove their activity.

Surprisingly, it has now been found that certain halogen-substitutedcompounds and their N-oxides and salts have biological properties andare particularly suitable for controlling animal pests, and cantherefore be employed particularly well in the agrochemical field and inthe animal health sector.

The halogen-substituted compounds according to the invention are definedby the general formulae (I) and (II)

in which

-   R¹ represents hydrogen, optionally substituted C₁-C₆-alkyl,    C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₃-C₇-cycloalkyl, C₁-C₆-alkylcarbonyl,    C₁-C₆-alkoxycarbonyl, aryl-(C₁-C₃)-alkyl, heteroaryl-(C₁-C₃)-alkyl,-   M¹ and M² each independently of one another represent hydrogen,    cyano or represent optionally mono- or polysubstituted C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,    C₁-C₆-alkoxycarbonyl, or-   M¹ and M² with the carbon atom to which they are attached form an    optionally substituted 3-, 4-, 5- or 6-membered ring which    optionally contains 0, 1 or 2 nitrogen atoms and/or 0, 1 or 2 oxygen    atoms and/or 0, 1 or 2 sulphur atoms,-   the chemical groupings-   A₁ represents CR² or nitrogen,-   A₂ represents CR³ or nitrogen,-   A₃ represents CR⁴ or nitrogen and-   A₄ represents CR⁵ or nitrogen,-   but where not more than three of the chemical groupings A₁ to A₄    simultaneously represent nitrogen;-   R², R³, R⁴ and R⁵ independently of one another represent hydrogen,    halogen, cyano, nitro, optionally substituted C₁-C₆-alkyl,    C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, N—C₁-C₆-alkoxy-imino-C₁-C₃-alkyl,    C₁-C₆-alkylsulphanyl, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl,    N—C₁-C₆-alkylamino or N,N-di-C₁-C₆-alkylamino;    -   if none of the groupings A₂ and A₃ represents nitrogen, R³ and        R⁴ together with the carbon atom to which they are attached may        form a 5- or 6-membered ring which contains 0, 1 or 2 nitrogen        atoms and/or 0 or 1 oxygen atom and/or 0 or 1 sulphur atom, or    -   if none of the groupings A₁ and A₂ represents nitrogen, R² and        R³ together with the carbon atom to which they are attached may        form a 6-membered ring which contains 0, 1 or 2 nitrogen atoms;-   W represents oxygen or sulphur;-   Q represents hydrogen, hydroxy, amino or one of the optionally    substituted groupings alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl,    heterocycloalkyl, cycloalkylalkyl, arylalkyl, heteroarylalkyl or    represents a grouping N-alkylamino, N-alkylcarbonylamino,    N,N-dialkylamino; or-   Q represents an unsaturated 6-membered carbocycle which is    optionally mono- or polysubstituted by V or an unsaturated 5- or    6-membered heterocyclic ring which is optionally mono- or    polysubstituted by V, where-   V independently of one another represent halogen, cyano, nitro,    optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy,    N-alkoxyiminoalkyl, alkylsulphanyl, alkylsulphinyl, alkylsulphonyl,    N,N-dialkylamino,-   T represents one of the 5-membered heteroaromatics T1-T8 listed    below, where the bond to the pyrazole head group is marked with an    asterisk,

where

-   R⁶ independently of one another represent halogen, cyano, nitro,    amino or optionally substituted C₁-C₆-alkyl, C₁-C₆-alkoxy,    C₁-C₆-alkylcarbonyl, C₁-C₆-alkylsulphanyl, C₁-C₆-alkylsulphinyl,    C₁-C₆-alkylsulphonyl, and-   n represents the values 0-2;-   Z¹ represents optionally substituted alkyl and cycloalkyl, and-   Z² represents hydrogen, halogen, cyano, nitro, amino or optionally    substituted alkyl, alkylcarbonyl, alkylsulphanyl, alkylsulphinyl,    alkylsulphonyl, and-   Z³ represents hydrogen or optionally substituted alkyl, cycloalkyl,    alkenyl, alkynyl, aryl or hetaryl.-   Furthermore, the radicals R¹, M¹, M² Q, V and R⁶ have the following    alternative meanings:-   R¹ represents hydrogen, optionally substituted C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₇-cycloalkyl, C₁-C₆-alkylcarbonyl,    C₁-C₆-alkoxycarbonyl, aryl-(C₁-C₃)-alkyl, heteroaryl-(C₁-C₃)-alkyl,-   M¹ and M² each independently of one another represent hydrogen,    cyano or represent optionally mono- or polysubstituted C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,    C₂-C₇-alkoxycarbonyl, or-   Q represents an unsaturated 6-membered carbocycle which is    optionally mono- or polysubstituted by V or an unsaturated 5- or    6-membered heterocyclic ring which is optionally mono- or    polysubstituted by V, where-   V independently of one another represent halogen, cyano, nitro,    optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy,    N-alkoxyiminoalkyl, alkylsulphanyl, alkylsulphinyl, alkylsulphonyl,    N,N-dialkylamino,-   R⁶ independently of one another represent halogen, cyano, nitro,    amino or optionally substituted C₁-C₆-alkyl, C₁-C₆-alkoxy,    C₁-C₆-alkylcarbonyl, C₁-C₆-alkylsulphanyl, C₁-C₆-alkylsulphinyl,    C₁-C₆-alkylsulphonyl.

General preference for the purpose of this application is always givento the compounds of the general formula (II), independently of thedegree of preference of the respective radical definitions.

Preference is given to compounds of the formulae (I) and (II)

in which

-   R¹ represents hydrogen, optionally substituted C₁-C₆-alkyl,    C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₃-C₇-cycloalkyl, C₁-C₆-alkylcarbonyl,    C₁-C₆-alkoxycarbonyl, aryl-(C₁-C₃)-alkyl, heteroaryl-(C₁-C₃)-alkyl,-   M¹ and M² each independently of one another represent hydrogen,    cyano or represent optionally mono- or polysubstituted C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,    C₁-C₆-alkoxycarbonyl, or-   M¹ and M² with the carbon atom to which they are attached form an    optionally substituted 3-, 4-, 5- or 6-membered ring which    optionally contains 0, 1 or 2 nitrogen atoms and/or 0, 1 or 2 oxygen    atoms and/or 0, 1 or 2 sulphur atoms,-   the chemical groupings-   A₁ represents CR² or nitrogen,-   A₂ represents CR³ or nitrogen,-   A₃ represents CR⁴ or nitrogen and-   A₄ represents CR⁵ or nitrogen,-   but where not more than three of the chemical groupings A₁ to A₄    simultaneously represent nitrogen;-   R², R³, R⁴ and R⁵ independently of one another represent hydrogen,    halogen, cyano, nitro, optionally substituted C₁-C₆-alkyl,    C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, N—C₁-C₆-alkoxyimino-C₁-C₃-alkyl,    C₁-C₆-alkylsulphanyl, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl,    N—C₁-C₆-alkylamino or N,N-di-C₁-C₆-alkylamino;    -   if none of the groupings A₂ and A₃ represents nitrogen, R³ and        R⁴ together with the carbon atom to which they are attached may        form a 5- or 6-membered ring which contains 0, 1 or 2 nitrogen        atoms and/or 0 or 1 oxygen atom and/or 0 or 1 sulphur atom, or    -   if none of the groupings A₁ and A₂ represents nitrogen, R² and        R³ together with the carbon atom to which they are attached may        form a 6-membered ring which contains 0, 1 or 2 nitrogen atoms;-   W represents oxygen or sulphur;-   Q represents hydrogen, formyl, hydroxy, amino or one of the    optionally substituted groupings C₁-C₆-alkyl, C₂-C₆-alkenyl,    C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₂-C₇-heterocycloalkyl,    C₁-C₄-alkoxy, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, aryl-(C₁-C₃)-alkyl,    heteroaryl-(C₁-C₃)-alkyl or represents a grouping    N—C₁-C₄-alkylamino, N—C₁-C₄-alkylcarbonylamino,    N,N-di-C₁-C₄-alkylamino; or-   Q represents an unsaturated 6-membered carbocycle which is    optionally mono- or polysubstituted by V or an unsaturated 5- or    6-membered heterocyclic ring which is optionally mono- or    polysubstituted by V, where-   V independently of one another represent halogen, cyano, nitro,    optionally substituted C₁-C₆-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,    C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, N—C₁-C₆-alkoxy-imino-C₁-C₃-alkyl,    C₁-C₆-alkylsulphanyl, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl,    N,N-di-(C₁-C₆-alkyl)amino;-   T represents one of the 5-membered heteroaromatics T1-T8 listed    below, where the bond to the pyrazole head group is marked with an    asterisk,

where

-   R⁶ independently of one another represent halogen, cyano, nitro,    amino or optionally halogen-substituted C₁-C₆-alkyl, C₁-C₆-alkoxy,    C₁-C₆-alkylcarbonyl, C₁-C₆-alkylsulphanyl, C₁-C₆-alkylsulphinyl,    C₁-C₆-alkylsulphonyl, and-   n represents the values 0-1;-   Z¹ represents optionally substituted C₁-C₆-haloalkyl,    C₃-C₆-halocycloalkyl, and-   Z² represents hydrogen, halogen, cyano, nitro, amino or optionally    substituted C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkylsulphanyl,    C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, and-   Z³ represents hydrogen or optionally substituted C₁-C₆-alkyl,    C₃-C₆-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, aryl or hetaryl.-   Preference is furthermore also given to compounds of the    formulae (I) and (II) in which the radicals below are alternatively    defined as follows:-   R¹ represents hydrogen, optionally substituted C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₇-cycloalkyl, C₁-C₆-alkylcarbonyl,    C₁-C₆-alkoxycarbonyl, aryl-(C₁-C₃)-alkyl, heteroaryl-(C₁-C₃)-alkyl,-   M¹ and M² each independently of one another represent hydrogen,    cyano or represent optionally mono- or polysubstituted C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,    C₂-C₇-alkoxycarbonyl, or-   R², R³, R⁴ and R⁵ independently of one another represent hydrogen,    halogen, cyano, nitro, optionally substituted C₁-C₆-alkyl,    C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, N—C₁-C₆-alkoxyimino-C₁-C₃-alkyl,    C₁-C₆-alkylsulphanyl, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl,    N—C₁-C₆-alkylamino or N,N-di-C₁-C₆-alkylamino;-   Q represents hydrogen, formyl, hydroxy, amino or one of the    optionally substituted groupings C₁-C₆-alkyl, C₂-C₆-alkenyl,    C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₅-heterocycloalkyl,    C₁-C₄-alkoxy, C₁-C₆-alkyl-C₃-C₆-cycloalkyl, aryl-(C₁-C₃)-alkyl,    heteroaryl-(C₁-C₃)-alkyl or represents a grouping    N—C₁-C₄-alkylamino, N—C₁-C₄-alkylcarbonylamino,    N,N-di-C₁-C₄-alkylamino; or-   Q represents an unsaturated 6-membered carbocycle which is    optionally mono- or polysubstituted by V or an unsaturated 5- or    6-membered heterocyclic ring which is optionally mono- or    polysubstituted by V, where-   V independently of one another represent halogen, cyano, nitro,    optionally substituted C₁-C₆-alkyl, C₁-C₄-alkenyl, C₁-C₄-alkynyl,    C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, N—C₁-C₆-alkoxyimino-C₁-C₃-alkyl,    C₁-C₆-alkylsulphanyl, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl,    N,N-di-(C₁-C₆-alkyl)amino;-   Z¹ represents optionally substituted C₁-C₆-haloalkyl,    C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, and-   Z³ represents hydrogen or optionally substituted alkyl, cycloalkyl,    alkenyl, alkynyl, aryl or hetaryl.

Particular preference is given to compounds of the formulae (I) and (II)

in which

-   R¹ represents hydrogen or represents C₁-C₆-alkyl, C₃-C₆-alkenyl,    C₃-C₆-alkynyl, C₃-C₇-cycloalkyl, C₁-C₆-alkylcarbonyl,    C₁-C₆-alkoxycarbonyl, aryl-(C₁-C₃)-alkyl, heteroaryl-(C₁-C₃)-alkyl    which are optionally mono- to heptasubstituted independently of one    another by fluorine, chlorine, cyano, C₁-C₆-alkoxy and    C₁-C₆-alkoxycarbonyl,-   M¹ represents hydrogen,-   M² represents hydrogen, cyano or represents C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₃-C₆-cycloalkyl, C₁-C₃-alkoxycarbonyl which are    optionally mono- to pentasubstituted independently of one another by    fluorine, chlorine, cyano or C₁-C₃-alkoxy,-   M¹ and M² with the carbon atom to which they are attached form an    optionally substituted 3-membered ring,-   the chemical groupings-   A₁ represents CR² or nitrogen,-   A₂ represents CR³ or nitrogen,-   A₃ represents CR⁴ or nitrogen and-   A₄ represents CR⁵ or nitrogen,-   but where not more than three of the chemical groupings A₁ to A₄    simultaneously represent nitrogen;-   R², R³, R⁴ and R⁵ independently of one another represent hydrogen,    fluorine, chlorine, bromine, iodine, cyano, nitro or represent    C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy,    N—C₁-C₆-alkoxyimino-C₁-C₃-alkyl, C₁-C₆-alkylsulphanyl,    C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, N—C₁-C₆-alkylamino or    N,N-di-C₁-C₆-alkylamino which are optionally mono- to    pentasubstituted independently of one another by fluorine, chlorine,    cyano, hydroxycarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyl or    phenyl;-   W represents oxygen or sulphur;-   Q represents hydrogen, amino or one of the groupings C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,    C₂-C₅-heterocycloalkyl, C₁-C₄-alkoxy, C₃-C₆-cycloalkyl-C₁-C₆-alkyl,    aryl-(C₁-C₃)-alkyl, heteroaryl-(C₁-C₃)-alkyl, N—C₁-C₄-alkylamino,    N—C₁-C₄-alkylcarbonylamino or N,N-di-C₁-C₄-alkylamino which are    optionally independently of one another mono- to pentasubstituted by    hydroxy, nitro, amino, fluorine, chlorine, C₁-C₆-alkyl,    C₁-C₆-alkoxy, cyano, hydroxycarbonyl, C₁-C₄-alkoxycarbonyl,    C₁-C₄-alkylcarbamoyl, C₃-C₇-cycloalkylcarbamoyl, phenyl; or-   Q represents aryl substituted by 0-4 substituents V or a 5- or    6-membered heteroaromatic substituted by 0-4 substituents V, where-   V independently of one another represent halogen, cyano, nitro,    optionally substituted C₁-C₆-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,    C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, N—C₁-C₆-alkoxyimino-C₁-C₃-alkyl,    C₁-C₆-alkylsulphanyl, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl,    N,N-di-(C₁-C₆-alkyl)amino;-   T represents one of the 5-membered heteroaromatics T1-T8 listed    below, where the bond to the pyrazole head group is marked with an    asterisk,

where

-   R⁶ independently of one another represent fluorine, chlorine,    bromine, iodine, cyano, nitro, amino or represents C₁-C₆-alkyl,    C₁-C₆-alkoxy, C₁-C₆-alkylcarbonyl, C₁-C₆-alkylsulphanyl,    C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl which are optionally    independently of one another mono- to pentasubstituted by fluorine    and/or chlorine, and-   n represents the values 0-1;-   Z¹ represents optionally substituted C₁-C₆-haloalkyl,    C₃-C₆-halocycloalkyl, and-   Z² represents hydrogen, fluorine, chlorine, bromine, iodine, cyano,    nitro, amino or represents C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl,    C₁-C₆-alkylsulphanyl, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl    which are optionally independently of one another mono- to    pentasubstituted by fluorine and/or chlorine, and-   Z³ represents hydrogen or optionally substituted C₁-C₆-alkyl,    C₃-C₆-cycloalkyl, C₃-C₄-alkenyl, C₃-C₄-alkynyl, aryl or hetaryl.

Particular preference is furthermore also given to compounds of theformulae (I) and (II) in which the radicals below are alternativelydefined as follows:

-   R⁶ independently of one another represent halogen, cyano, nitro,    amino or optionally independently of one another mono- to    pentahalogen-substituted C₁-C₆-alkyl, C₁-C₆-alkoxy,    C₁-C₆-alkylcarbonyl, C₁-C₆-alkylsulphanyl, C₁-C₆-alkylsulphinyl,    C₁-C₆-alkylsulphonyl, and-   Z¹ represents optionally substituted C₁-C₆-alkyl, C₃-C₆-cycloalkyl,    and-   Z² represents hydrogen, halogen, cyano, nitro, amino or represents    C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkylsulphanyl,    C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl which are optionally    independently of one another mono- to pentasubstituted by fluorine    and/or chlorine, and-   Z³ represents hydrogen or optionally substituted C₁-C₆-alkyl,    C₃-C₆-cycloalkyl, C₁-C₄-alkenyl, C₁-C₄-alkynyl, aryl or hetaryl.

Very particular preference is given to compounds of the formulae (I) and(II)

in which

-   R¹ represents hydrogen or represents C₁-C₄-alkyl, C₃-C₄-alkenyl,    C₃-C₄-alkynyl, C₃-C₆-cycloalkyl, C₁-C₄-alkylcarbonyl,    C₁-C₄-alkoxycarbonyl, aryl-(C₁-C₂)-alkyl, heteroaryl-(C₁-C₂)-alkyl    which are optionally mono- to pentasubstituted independently of one    another by fluorine, chlorine, cyano, C₁-C₄-alkoxy and    C₁-C₄-alkoxycarbonyl,-   M¹ represents hydrogen,-   M² represents hydrogen or represents C₁-C₃-alkyl, C₂-C₆-alkenyl,    C₃-C₆-cycloalkyl, C₁-C₃-alkoxycarbonyl which are optionally mono- to    pentasubstituted independently of one another by halogen, cyano,    alkoxy and alkoxycarbonyl,-   M¹ and M² with the carbon atom to which they are attached form an    optionally substituted 3-membered ring,-   the chemical groupings-   A₁ represents CR² or nitrogen,-   A₂ represents CR³ or nitrogen,-   A₃ represents CR⁴ or nitrogen and-   A₄ represents CR⁵ or nitrogen,-   but where not more than three of the chemical groupings A₁ to A₄    simultaneously represent nitrogen;-   R², R³, R⁴ and R⁵ independently of one another represent hydrogen,    fluorine, chlorine, bromine, cyano, nitro, or represent C₁-C₄-alkyl,    C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, N—C₁-C₄-alkoxyimino-C₁-C₂-alkyl,    C₁-C₄-alkylsulphanyl, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,    N—C₁-C₄-alkylamino or N,N-di-C₁-C₄-alkylamino which are optionally    independently of one another mono- to pentasubstituted by hydroxy,    nitro, amino, fluorine, chlorine, C₁-C₄-alkoxy, cyano,    hydroxycarbonyl;-   W represents oxygen or sulphur;-   Q represents hydrogen, amino or represents one of the groupings    C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,    C₂-C₅-heterocycloalkyl, C₁-C₄-alkoxy, C₃-C₆-cycloalkyl-C₁-C₆-alkyl,    aryl-(C₁-C₃)-alkyl, heteroaryl-(C₁-C₃)-alkyl, N—C₁-C₄-alkylamino,    N—C₁-C₄-alkylcarbonylamino or N,N-di-C₁-C₄-alkylamino which are    optionally independently of one another mono- to pentasubstituted by    hydroxy, nitro, amino, halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, cyano,    hydroxycarbonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbamoyl,    C₃-C₆-cycloalkylcarbamoyl, phenyl; or-   Q represents aryl substituted by 0, 1, 2, 3 or 4 substituents V or a    5- or 6-membered heteroaromatic substituted by 0, 1, 2, 3 or 4    substituents V, where-   V independently of one another represent fluorine, chlorine,    bromine, iodine, cyano, nitro or represent C₁-C₆-alkyl,    C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy,    N—C₁-C₆-alkoxyimino-C₁-C₃-alkyl, C₁-C₆-alkylsulphanyl,    C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl,    N,N-di-(C₁-C₆-alkyl)amino which are optionally independently of one    another mono- to pentasubstituted by hydroxy, nitro, amino,    fluorine, chlorine, bromine, iodine, C₁-C₄-alkyl, C₁-C₄-alkoxy,    cyano, hydroxycarbonyl;-   T represents one of the 5-membered heteroaromatics T1-T8 listed    below, where the bond to the pyrazole head group is marked with an    asterisk,

where

-   R⁶ independently of one another represent fluorine, chlorine, cyano,    nitro, amino or represents C₁-C₆-alkyl, C₁-C₆-alkoxy,    C₁-C₆-alkylcarbonyl, C₁-C₆-alkylsulphanyl, C₁-C₆-alkylsulphinyl,    C₁-C₆-alkylsulphonyl which are optionally mono- to pentasubstituted    by fluorine and/or chlorine, and-   n represents the values 0-1;-   Z¹ represents C₁-C₄-haloalkyl, C₃-C₆-halocycloalkyl optionally mono-    to disubstituted by C₁-C₄-alkoxy, cyano, hydroxycarbonyl,    C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbamoyl,    C₃-C₆-cycloalkylcarbamoyl, phenyl, and-   Z² represents hydrogen, fluorine, chlorine, bromine, iodine, cyano,    nitro, amino or represents C₁-C₄-alkyl, C₁-C₄-alkylcarbonyl,    C₁-C₄-alkylsulphanyl, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl    which are optionally independently of one another mono- to    trisubstituted by hydroxy, nitro, amino, fluorine, chlorine,    C₁-C₄-alkoxy, cyano, hydroxycarbonyl, C₁-C₄-alkoxycarbonyl,    C₁-C₄-alkylcarbamoyl, C₃-C₆-cycloalkylcarbamoyl, phenyl, and-   Z³ represents hydrogen or represents C₁-C₄-alkyl, C₃-C₆-cycloalkyl,    C₃-C₄-alkenyl, C₃-C₄-alkynyl, phenyl and hetaryl which are    optionally independently of one another mono- to trisubstituted by    hydroxy, nitro, amino, C₁-C₄-alkoxy, cyano, fluorine, chlorine,    hydroxycarbonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbamoyl,    C₃-C₆-cycloalkylcarbamoyl, phenyl.

Especially preferred are compounds of the formulae (I) and (II)

in which

-   R¹ represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl,    isobutyl, s-butyl, t-butyl, methoxymethyl, ethoxymethyl,    propoxymethyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl,    isopropylcarbonyl, n-butylcarbonyl, isobutylcarbonyl,    s-butylcarbonyl, t-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl,    n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl,    isobutoxycarbonyl, s-butoxycarbonyl, t-butoxycarbonyl, cyanomethyl,    2-cyanoethyl, benzyl, 4-methoxybenzyl, pyrid-2-ylmethyl,    pyrid-3-ylmethyl, pyrid-4-ylmethyl, 6-chloropyrid-3-ylmethyl;-   M¹ represents hydrogen,-   M² represents hydrogen, methyl, ethyl, difluoromethyl,    trichloromethyl, dichlorofluoromethyl, trifluoromethyl, cyclopropyl,    cyclobutyl, methoxycarbonyl, ethoxycarbonyl,-   M¹ and M² with the carbon atom to which they are attached form a    3-membered carbocycle, the chemical groupings-   A₁ represents CR² or nitrogen,-   A₂ represents CR³ or nitrogen,-   A₃ represents CR⁴ or nitrogen and-   A₄ represents CR⁵ or nitrogen,-   but where not more than three of the chemical groupings A₁ to A₄    simultaneously represent nitrogen;-   R² and R⁵ independently of one another represent hydrogen, methyl,    fluorine or chlorine and-   R³ and R⁴ independently of one another represent hydrogen, fluorine,    chlorine, bromine, iodine, cyano, nitro, methyl, ethyl,    fluoromethyl, difluoromethyl, chlorodifluoromethyl, trifluoromethyl,    2,2,2-trifluoroethyl, methoxy, ethoxy, n-propoxy, 1-methylethoxy,    fluoromethoxy, difluoromethoxy, chlorodifluoromethoxy,    dichlorofluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy,    2-chloro-2,2-difluoroethoxy, pentafluoroethoxy,    N-methoxyiminomethyl, 1-(N-methoxyimino)ethyl, methylsulphanyl,    trifluoromethylsulphanyl, methylsulphonyl, methylsulphinyl,    trifluoromethylsulphonyl, trifluoromethylsulphinyl;-   W represents oxygen or sulphur;-   Q represents hydrogen, methyl, ethyl, n-propyl, isopropyl, t-butyl,    1-methylpropyl, n-butyl, 2-methylpropyl, 2-methylbutyl,    hydroxymethyl, 2-hydroxyethyl, 2-hydroxypropyl, cyanomethyl,    2-cyanoethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl,    2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1-trifluoromethylethyl,    2,2-difluoropropyl, 3,3,3-trifluoropropyl,    2,2-dimethyl-3-fluoropropyl, cyclopropyl, 1-cyanocyclopropyl,    cyclopropylmethyl, cyclobutyl, cyclopentyl, cyclohexyl,    1-cyclopropylethyl, bis(cyclopropyl)methyl,    2,2-dimethylcyclopropylmethyl, 2-phenylcyclopropyl,    2,2-dichlorocyclopropyl, trans-2-chlorocyclopropyl,    cis-2-chlorocyclopropyl, 2,2-difluorocyclopropyl,    trans-2-fluorocyclopropyl, cis-2-fluorocyclopropyl,    trans-4-hydroxycyclohexyl, 4-trifluoromethylcyclohexyl, ethenyl,    1-methylethenyl, prop-1-enyl, 2-methylprop-1-enyl,    3-methylbut-1-enyl, 3,3,3-trifluoroprop-1-enyl, 1-ethylethenyl,    1-methylprop-1-enyl, prop-2-ynyl, 3-fluoroprop-2-enyl, oxetan-3-yl,    thietan-3-yl, 1-oxidothietan-3-yl, 1,1-dioxidothietan-3-yl,    tetrahydrofuran-3-yl, 1,1-dioxidotetrahydrothiophen-3-yl,    isoxazol-3-ylmethyl, 1,2,4-triazol-3-ylmethyl,    3-methyloxetan-3-ylmethyl, benzyl, 2,6-difluorophenylmethyl,    3-fluorophenylmethyl, 2-fluorophenylmethyl,    2,5-difluorophenylmethyl, 1-phenylethyl, 4-chlorophenylethyl,    2-trifluoromethylphenylethyl, 1-pyridin-2-ylethyl,    pyridin-2-ylmethyl, 5-fluoropyridin-2-ylmethyl,    (6-chloropyridin-3-yl)methyl, pyrimidin-2-ylmethyl,    thiophen-2-yl-methyl, 2-ethoxyethyl, 2-methoxyethyl,    1-(methylsulphanyl)ethyl, 2-(methylsulphanyl)ethyl,    1-methyl-2-(ethylsulphanyl)ethyl,    2-methyl-1-(methylsulphanyl)propan-2-yl, methoxycarbonyl,    ethoxycarbonyl, methoxycarbonylmethyl, NH₂, N-ethylamino,    N-allylamino, N,N-dimethylamino, N,N-diethylamino, methoxy, ethoxy,    propoxy, isopropoxy, tert-butoxy; or-   Q represents phenyl, naphthyl, pyridazine, pyrazine, pyrimidine,    triazine, pyridine, pyrazole, thiazole, isothiazole, oxazole,    isoxazole, triazole, imidazole, furan, thiophene, pyrrole,    oxadiazole, thiadiazole substituted by 0, 1, 2 or 3 substituents V,    where-   V independently of one another represent fluorine, chlorine,    bromine, iodine, cyano, nitro, methyl, ethyl, difluoromethyl,    trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl,    trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl,    2,2,2-trifluoroethyl, 1,2,2,2-tetrafluoroethyl,    1-chloro-1,2,2,2-tetrafluoroethyl, 2,2,2-trichloroethyl,    2-chloro-2,2-difluoroethyl, 1,1-difluoroethyl, pentafluoroethyl,    heptafluoro-n-propyl, heptafluoroisopropyl, nonafluoro-n-butyl,    cyclopropyl, cyclobutyl, methoxy, ethoxy, n-propoxy, 1-methylethoxy,    fluoromethoxy, difluoromethoxy, chlorodifluoromethoxy,    dichlorofluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy,    2-chloro-2,2-difluoroethoxy, pentafluoroethoxy,    N-methoxyiminomethyl, 1-(N-methoxyimino)ethyl, methylsulphanyl,    methylsulphonyl, methylsulphinyl, trifluoromethylsulphonyl,    trifluoromethylsulphinyl, trifluoromethylsulphanyl,    N,N-dimethylamino;-   T represents one of the 5-membered heteroaromatics T1-T8 listed    below, where the bond to the pyrazole head group is marked with an    asterisk,

-   where-   R⁶ independently of one another represent fluorine, chlorine, cyano,    nitro, amino, methyl, ethyl, propyl, 1-methylethyl, tert-butyl,    trifluoromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy,    2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, methylcarbonyl,    ethylcarbonyl, trifluoromethylcarbonyl, methylsulphanyl,    methylsulphinyl, methylsulphonyl, trifluoromethylsulphonyl,    trifluoromethylsulphanyl, trifluoromethylsulphinyl, and-   n represents the values 0-1;-   Z¹ represents difluoromethyl, trichloromethyl, chlorodifluoromethyl,    dichlorofluoromethyl, trifluoromethyl, bromodichloromethyl,    1-fluoroethyl, 1-fluoro-1-methylethyl, 2-fluoroethyl,    2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,2,2,2-tetrafluoroethyl,    1-chloro-1,2,2,2-tetrafluoroethyl, 2,2,2-trichloroethyl,    2-chloro-2,2-difluoroethyl, 1,1-difluoroethyl, pentafluoroethyl,    heptafluoro-n-propyl, heptafluoroisopropyl, nonafluoro-n-butyl,    cyclopropyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl,    1-bromocyclopropyl, 1-cyanocyclopropyl,    1-trifluoromethylcyclopropyl, cyclobutyl or    2,2-difluoro-1-methylcyclopropyl, and-   Z² represents hydrogen, fluorine, chlorine, bromine, iodine, cyano,    nitro, amino, methyl, ethyl, 1,1-t-butyl, difluoromethyl,    trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl,    trifluoromethyl, bromodichloromethyl, 1-fluoroethyl,    1-fluoro-1-methylethyl, 2-fluoroethyl, 2,2-difluoroethyl,    2,2,2-trifluoroethyl, 1,2,2,2-tetrafluorethyl,    1-chloro-1,2,2,2-tetrafluoroethyl, 2,2,2-trichloroethyl,    2-chloro-2,2-difluoroethyl, 1,1-difluoroethyl, pentafluoroethyl,    heptafluoro-n-propyl, heptafluoroisopropyl, nonafluoro-n-butyl,    methylsulphanyl, methylsulphinyl, methylsulphonyl, ethylthio,    ethylsulphinyl, ethylsulphonyl, trifluoromethylsulphanyl,    trifluoromethylsulphinyl, trifluoromethylsulphonyl,    chlorodifluoromethylsulphanyl, chlorodifluoromethylsulphinyl,    chlorodifluoromethylsulphonyl, dichlorofluoromethylsulphanyl,    dichlorofluoromethylsulphinyl, dichlorofluoromethylsulphonyl and-   Z³ represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl,    isobutyl, s-butyl, t-butyl, 1-propenyl, 1-propynyl, 1-butyryl,    difluoromethyl, trichloromethyl, chlorodifluoromethyl,    dichlorofluoromethyl, trifluoromethyl, 1-fluoroethyl,    1-fluoro-1-methylethyl, 2-fluoroethyl, 2,2-difluoroethyl,    2,2,2-trifluoroethyl, phenyl, 2-chlorophenyl, 3-chlorophenyl,    4-chlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl,    3,4-dichlorophenyl, 2,6-dichlorophenyl,    2,6-dichloro-4-trifluoromethylphenyl,    3-chloro-5-trifluoromethylpyridin-2-yl.

Special preference is furthermore also given to compounds of theformulae (I) and (II) in which the radicals below are alternativelydefined as follows:

-   R¹ represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl,    isobutyl, s-butyl, t-butyl, methoxymethyl, ethoxymethyl,    propoxymethyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl,    isopropylcarbonyl, s-butylcarbonyl, t-butylcarbonyl,    methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl,    isopropoxycarbonyl, s-butoxycarbonyl, t-butoxycarbonyl, cyanomethyl,    2-cyanoethyl, benzyl, 4-methoxybenzyl, pyrid-2-ylmethyl,    pyrid-3-ylmethyl, pyrid-4-ylmethyl, 6-chloropyrid-3-ylmethyl;-   M² represents hydrogen, C₁-C₃-alkyl, C₂-C₃-alkenyl,    C₃-C₆-cycloalkyl, C₁-C₃-alkoxycarbonyl, cyano or cyano-C₁-C₂-alkyl,-   Q represents hydrogen, methyl, ethyl, n-propyl, 1-methylethyl,    1,1-dimethylethyl, 1-methylpropyl, n-butyl, 2-methylpropyl,    2-methylbutyl, hydroxymethyl, 2-hydroxypropyl, cyanomethyl,    2-cyanoethyl, 2-fluoroethyl, 2,2-difluoroethyl,    2,2,2-trifluoroethyl, 1-trifluoromethylethyl, 2,2-difluoropropyl,    3,3,3-trifluoropropyl, 2,2-dimethyl-3-fluoropropyl, cyclopropyl,    1-cyanocyclopropyl, 1-methoxycarbonylcyclopropyl,    1-(N-methylcarbamoyl)cyclopropyl,    1-(N-cyclopropylcarbamoyl)cyclopropyl, cyclopropylmethyl,    cyclobutyl, cyclopentyl, cyclohexyl, 1-cyclopropylethyl,    bis(cyclopropyl)methyl, 2,2-dimethylcyclopropylmethyl,    2-phenylcyclopropyl, 2,2-dichlorocyclopropyl,    trans-2-chlorocyclopropyl, cis-2-chlorocyclopropyl,    2,2-difluorocyclopropyl, trans-2-fluorocyclopropyl,    cis-2-fluorocyclopropyl, trans-4-hydroxycyclohexyl,    4-trifluoromethylcyclohexyl, prop-2-enyl, 2-methylprop-2-enyl,    prop-2-ynyl, 1,1-dimethylbut-2-ynyl, 3-chloroprop-2-enyl,    3,3-dichloroprop-2-enyl, 3,3-dichloro-1,1-dimethylprop-2-enyl,    phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, oxetan-3-yl,    thietan-3-yl, 1-oxidothietan-3-yl, 1,1-dioxidothietan-3-yl,    isoxazol-3-ylmethyl, 1,2,4-triazol-3-ylmethyl,    3-methyloxetan-3-ylmethyl, benzyl, 2,6-difluorophenylmethyl,    3-fluorophenylmethyl, 2-fluorophenylmethyl,    2,5-difluorophenylmethyl, 1-phenylethyl, 4-chlorophenylethyl,    2-trifluormethylphenylethyl, 1-pyridin-2-ylethyl,    pyridin-2-ylmethyl, 5-fluoropyridin-2-ylmethyl,    (6-chloropyridin-3-yl)methyl, pyrimidin-2-ylmethyl, methoxy,    2-ethoxyethyl, 2-(methylsulphanyl)ethyl,    1-methyl-2-(ethylsulphanyl)ethyl,    2-methyl-1-(methylsulphanyl)propan-2-yl, methoxycarbonyl,    methoxycarbonylmethyl, NH₂, N-ethylamino, N-allylamino,    N,N-dimethylamino, N,N-diethylamino; or-   Q represents phenyl, naphthyl, pyridazine, pyrazine, pyrimidine,    triazine, pyridine, pyrazole, thiazole, isothiazole, oxazole,    isoxazole, triazole, imidazole, furan, thiophene, pyrrole,    oxadiazole, thiadiazole substituted by 0-4 substituents V, where-   V independently of one another represent fluorine, chlorine,    bromine, iodine, cyano, nitro, methyl, ethyl, difluoromethyl,    trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl,    trifluoromethyl, chloromethyl, bromomethyl, 1-fluoroethyl,    2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,    1,2,2,2-tetrafluoroethyl, 1-chloro-1,2,2,2-tetrafluoroethyl,    2,2,2-trichloroethyl, 2-chloro-2,2-difluoroethyl, 1,1-difluoroethyl,    pentafluoroethyl, pentafluoro-tert-butyl, heptafluoro-n-propyl,    heptafluoroisopropyl, nonafluoro-n-butyl, cyclopropyl, cyclobutyl,    methoxy, ethoxy, n-propoxy, 1-methylethoxy, fluoromethoxy,    difluoromethoxy, chlorodifluoromethoxy, dichlorofluoromethoxy,    trifluoromethoxy, 2,2,2-trifluoroethoxy,    2-chloro-2,2-difluoroethoxy, pentafluoroethoxy,    N-methoxyiminomethyl, 1-(N-methoxyimino)ethyl, methylsulphanyl,    methylsulphonyl, methylsulphinyl, trifluoromethylsulphonyl,    trifluoromethylsulphinyl, trifluoromethylsulphanyl,    N,N-dimethylamino;-   R⁶ independently of one another represent halogen, cyano, nitro,    amino, methyl, ethyl, 1-methylethyl, tert-butyl, trifluoromethyl,    difluoromethyl, methoxy, ethoxy, trifluoromethoxy,    2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, methylcarbonyl,    ethylcarbonyl, trifluoromethylcarbonyl, methylsulphanyl,    methylsulphinyl, methylsulphonyl, trifluoromethylsulphonyl,    trifluoromethylsulphanyl, trifluoromethylsulphinyl, and-   n represents the values 0-1;-   Z¹ represents methyl, ethyl, 1,1-dimethylethyl, difluoromethyl,    trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl,    trifluoromethyl, bromodichloromethyl, chloromethyl, bromomethyl,    1-fluoroethyl, 1-fluoro-1-methylethyl, 2-fluoroethyl,    2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,2,2,2-tetrafluoroethyl,    1-chloro-1,2,2,2-tetrafluoroethyl, 2,2,2-trichloroethyl,    2-chloro-2,2-difluoroethyl, 1,1-difluoroethyl, pentafluoroethyl,    pentafluoro-tert-butyl, heptafluoro-n-propyl, heptafluoroisopropyl,    nonafluoro-n-butyl, cyclopropyl, 1-chlorocyclopropyl,    1-fluorocyclopropyl, 1-bromocyclopropyl, 1-cyanocyclopropyl,    1-trifluoromethylcyclopropyl, cyclobutyl and    2,2-difluoro-1-methylcyclopropyl, and-   Z² represents hydrogen, halogen, cyano, nitro, amino, methyl, ethyl,    1,1-dimethylethyl, difluoromethyl, trichloromethyl,    chlorodifluoromethyl, dichlorofluoromethyl, trifluoromethyl,    bromodichloromethyl, chloromethyl, bromomethyl, 1-fluoroethyl,    1-fluoro-1-methylethyl, 2-fluoroethyl, 2,2-difluoroethyl,    2,2,2-trifluoroethyl, 1,2,2,2-tetrafluoroethyl,    1-chloro-1,2,2,2-tetrafluoroethyl, 2,2,2-trichloroethyl,    2-chloro-2,2-difluoroethyl, 1,1-difluoroethyl, pentafluoroethyl,    pentafluoro-t-butyl, heptafluoro-n-propyl, heptafluoroisopropyl,    nonafluoro-n-butyl, methylsulphanyl, methylsulphinyl,    methylsulphonyl, ethylthio, ethylsulphinyl, ethylsulphonyl,    trifluoromethylsulphanyl, trifluoromethylsulphinyl,    trifluoromethylsulphonyl, chlorodifluoromethylsulphanyl,    chlorodifluoromethylsulphinyl, chlorodifluoromethylsulphonyl,    dichlorofluoromethylsulphanyl, dichlorofluoromethylsulphinyl,    dichlorofluoromethylsulphonyl and-   Z³ represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl,    isobutyl, s-butyl, t-butyl, ethenyl, 1-propenyl, 2-propenyl,    1-propynyl, 1-butynyl, difluoromethyl, trichloromethyl,    chlorodifluoromethyl, dichlorofluoromethyl, trifluoromethyl,    chloromethyl, bromomethyl, 1-fluoroethyl, 1-fluoro-1-methylethyl,    2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, phenyl,    2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,5-dichlorophenyl,    3,4-dichlorophenyl, 2,6-dichlorophenyl,    2,6-dichloro-4-trifluoromethylphenyl,    3-chloro-5-trifluoromethylpyridin-2-yl.

Very especially preferred compounds for the purpose of the invention arethose of the general formulae (I) and (II) in which

-   Z¹ represents trifluoromethyl, 1-chlorocyclopropyl,    1-fluorocyclopropyl or pentafluoroethyl,-   Z² represents trifluoromethyl, nitro, methylsulphanyl,    methylsulphinyl, methylsulphonyl, fluorine, chlorine, bromine, cyano    or iodine,-   Z³ represents methyl, ethyl, n-propyl or hydrogen,-   R¹ represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl,    isobutyl, s-butyl, t-butyl, methoxymethyl, ethoxymethyl,    propoxymethyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl,    isopropylcarbonyl, n-butylcarbonyl, isobutylcarbonyl,    s-butylcarbonyl, t-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl,    n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl,    isobutoxycarbonyl, s-butoxycarbonyl, t-butoxycarbonyl, cyanomethyl,    2-cyanoethyl, benzyl, 4-methoxybenzyl, pyrid-2-ylmethyl,    pyrid-3-ylmethyl, pyrid-4-ylmethyl, 6-chloropyrid-3-ylmethyl,-   M¹ represents hydrogen;-   M² represents hydrogen or methyl;-   M¹ and M² with the carbon atom to which they are attached form a    3-membered carbocycle,-   A¹ and A⁴ represent CH,-   A² represents CH or N,-   A₃ represents CR⁴ and-   R⁴ represents methyl, ethyl, fluorine, chlorine, bromine or iodine,-   T represents one of the 5-membered heteroaromatics T1-T8 listed    below, where the bond to the pyrazole head group is marked with an    asterisk,

where

-   R⁶ represents hydrogen, methyl, ethyl, 2-methylethyl,    2,2-dimethylethyl, fluorine, chlorine, bromine, iodine, nitro,    trifluoromethyl, amino,-   W represents oxygen and-   Q represents hydrogen, methyl, ethyl, n-propyl, 1-methylethyl,    1,1-dimethylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,    2-methylbutyl, hydroxymethyl, 2-hydroxypropyl, cyanomethyl,    2-cyanoethyl, 2-fluoroethyl, 2,2-difluoroethyl,    2,2,2-trifluoroethyl, 1-trifluoromethylethyl, 2,2-difluoropropyl,    3,3,3-trifluoropropyl, 2,2-dimethyl-3-fluoropropyl, cyclopropyl,    cyclopropylmethyl, cyclobutyl, cyclopentyl, cyclohexyl,    1-cyclopropylethyl, bis(cyclopropyl)methyl,    2,2-dimethylcyclopropylmethyl, 2-phenylcyclopropyl,    2,2-dichlorocyclopropyl, trans-2-chlorocyclopropyl,    cis-2-chlorocyclopropyl, 2,2-difluorocyclopropyl,    trans-2-fluorocyclopropyl, cis-2-fluorocyclopropyl,    trans-4-hydroxycyclohexyl, 4-trifluoromethylcyclohexyl, ethenyl,    1-methylethenyl, prop-1-enyl, 2-methylprop-1-enyl,    3-methylbut-1-enyl, 3,3,3-trifluoroprop-1-enyl, 1-ethylethenyl,    1-methylprop-1-enyl, prop-2-ynyl, 3-fluoroprop-2-enyl, oxetan-3-yl,    thietan-3-yl, 1-oxidothietan-3-yl, 1,1-dioxidothietan-3-yl,    isoxazol-3-ylmethyl, 1,2,4-triazol-3-ylmethyl,    3-methyloxetan-3-ylmethyl, benzyl, 2,6-difluorophenylmethyl,    3-fluorophenylmethyl, 2-fluorophenylmethyl,    2,5-difluorophenylmethyl, 1-phenylethyl, 4-chlorophenylethyl,    2-trifluormethylphenylethyl, 1-pyridin-2-ylethyl,    pyridin-2-ylmethyl, (6-chloropyridin-3-yl)methyl,    5-fluoropyridin-2-ylmethyl, pyrimidin-2-ylmethyl, methoxy,    2-ethoxyethyl, 2-(methylsulphanyl)ethyl,    1-methyl-2-(ethylsulphanyl)ethyl,    2-methyl-1-(methylsulphanyl)propan-2-yl, methoxycarbonyl,    methoxycarbonylmethyl, NH₂, N-ethylamino, N-allylamino,    N,N-dimethylamino, N,N-diethylamino, methoxy, ethoxy, propoxy,    isopropoxy, tert-butoxy; or-   Q represents phenyl, naphthyl, pyridazine, pyrazine, pyrimidine,    triazine, pyridine, pyrazole, thiazole, isothiazole, oxazole,    isoxazole, triazole, imidazole, furan, thiophene, pyrrole,    oxadiazole, thiadiazole substituted by 0, 1, 2 or 3 substituents V,    where-   V independently of one another represent fluorine, chlorine,    bromine, iodine, cyano, nitro, methyl, ethyl, difluoromethyl,    trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl,    trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl,    2,2,2-trifluoroethyl, 1,2,2,2-tetrafluoroethyl,    1-chloro-1,2,2,2-tetrafluoroethyl, 2,2,2-trichloroethyl,    2-chloro-2,2-difluoroethyl, 1,1-difluoroethyl, pentafluoroethyl,    heptafluoro-n-propyl, heptafluoroisopropyl, nonafluoro-n-butyl,    cyclopropyl, cyclobutyl, methoxy, ethoxy, n-propoxy, 1-methylethoxy,    fluoromethoxy, difluoromethoxy, chlorodifluoromethoxy,    dichlorofluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy,    2-chloro-2,2-difluoroethoxy, pentafluoroethoxy,    N-methoxyiminomethyl, 1-(N-methoxyimino)ethyl, methylsulphanyl,    methylsulphonyl, methylsulphinyl, trifluoromethylsulphonyl,    trifluoromethylsulphinyl, trifluoromethylsulphanyl,    N,N-dimethylamino.

Very especially preferred compounds are furthermore also those in whichthe radicals below are alternatively defined as follows:

-   R¹ represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl,    isobutyl, s-butyl, t-butyl, methoxymethyl, ethoxymethyl,    propoxymethyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl,    isopropylcarbonyl, s-butylcarbonyl, t-butylcarbonyl,    methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl,    isopropoxycarbonyl, s-butoxycarbonyl, t-butoxycarbonyl, cyanomethyl,    2-cyanoethyl, benzyl, 4-methoxybenzyl, pyrid-2-ylmethyl,    pyrid-3-ylmethyl, pyrid-4-ylmethyl, 6-chloropyrid-3-ylmethyl,-   A¹, A² and A⁴ represent CH,-   R⁴ represents fluorine, chlorine, bromine or iodine,-   Q represents hydrogen, methyl, ethyl, n-propyl, 1-methylethyl,    1,1-dimethylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,    2-methylbutyl, hydroxymethyl, 2-hydroxypropyl, cyanomethyl,    2-cyanoethyl, 2-fluoroethyl, 2,2-difluoroethyl,    2,2,2-trifluoroethyl, 1-trifluoromethylethyl, 2,2-difluoropropyl,    3,3,3-trifluoropropyl, 2,2-dimethyl-3-fluoropropyl, cyclopropyl,    1-cyanocyclopropyl, 1-methoxycarbonylcyclopropyl,    1-(N-methylcarbamoyl)cyclopropyl,    1-(N-cyclopropylcarbamoyl)cyclopropyl, cyclopropylmethyl,    cyclobutyl, cyclopentyl, cyclohexyl, 1-cyclopropylethyl,    bis(cyclopropyl)methyl, 2,2-dimethylcyclopropylmethyl,    2-phenylcyclopropyl, 2,2-dichlorocyclopropyl,    trans-2-chlorocyclopropyl, cis-2-chlorocyclopropyl,    2,2-difluorocyclopropyl, trans-2-fluorocyclopropyl,    cis-2-fluorocyclopropyl, trans-4-hydroxycyclohexyl,    4-trifluoromethylcyclohexyl, prop-2-enyl, 2-methylprop-2-enyl,    prop-2-ynyl, 1,1-dimethylbut-2-ynyl, 3-chloroprop-2-enyl,    3,3-dichloroprop-2-enyl, 3,3-dichloro-1,1-dimethylprop-2-enyl,    phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, oxetan-3-yl,    thietan-3-yl, 1-oxidothietan-3-yl, 1,1-dioxidothietan-3-yl,    isoxazol-3-ylmethyl, 1,2,4-triazol-3-ylmethyl,    3-methyloxetan-3-ylmethyl, benzyl, 2,6-difluorophenylmethyl,    3-fluorophenylmethyl, 2-fluorophenylmethyl,    2,5-difluorophenylmethyl, 1-phenylethyl, 4-chlorophenylethyl,    2-trifluormethylphenylethyl, 1-pyridin-2-ylethyl,    pyridin-2-ylmethyl, (6-chloropyridin-3-yl)methyl,    5-fluoropyridin-2-ylmethyl, pyrimidin-2-ylmethyl, methoxy,    2-ethoxyethyl, 2-(methylsulphanyl)ethyl,    1-methyl-2-(ethylsulphanyl)ethyl,    2-methyl-1-(methylsulphanyl)propan-2-yl, methoxycarbonyl,    methoxycarbonylmethyl, NH₂, N-ethylamino, N-allylamino,    N,N-dimethylamino, N,N-diethylamino; or-   Q represents phenyl, naphthyl, pyridazine, pyrazine, pyrimidine,    triazine, pyridine, pyrazole, thiazole, isothiazole, oxazole,    isoxazole, triazole, imidazole, furan, thiophene, pyrrole,    oxadiazole, thiadiazole substituted by 0-4 substituents V, where-   V independently of one another represent fluorine, chlorine,    bromine, iodine, cyano, nitro, methyl, ethyl, difluoromethyl,    trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl,    trifluoromethyl, chloromethyl, bromomethyl, 1-fluoroethyl,    2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,    1,2,2,2-tetrafluoroethyl, 1-chloro-1,2,2,2-tetrafluoroethyl,    2,2,2-trichloroethyl, 2-chloro-2,2-difluoroethyl, 1,1-difluoroethyl,    pentafluoroethyl, pentafluoro-tert-butyl, heptafluoro-n-propyl,    heptafluoroisopropyl, nonafluoro-n-butyl, cyclopropyl, cyclobutyl,    methoxy, ethoxy, n-propoxy, 1-methylethoxy, fluoromethoxy,    difluoromethoxy, chlorodifluoromethoxy, dichlorofluoromethoxy,    trifluoromethoxy, 2,2,2-trifluoroethoxy,    2-chloro-2,2-difluoroethoxy, pentafluoroethoxy,    N-methoxyiminomethyl, 1-(N-methoxyimino)ethyl, methylsulphanyl,    methylsulphonyl, methylsulphinyl, trifluoromethylsulphonyl,    trifluoromethylsulphinyl, trifluoromethylsulphanyl,    N,N-dimethylamino;

Especially emphasized compounds for the purpose of the invention arethose of the general formulae (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig),(Ih) in which the radicals A₁-A₄, n, W, Q, R¹, R⁶, M¹, M² and Z¹-Z³ havethe meanings given above.

Especially emphasized compounds for the purpose of the invention arefurthermore those of the general formulae (IIa), (IIb), (IIc), (IId),(IIe), (IIf), (IIg), (IIh) in which the radicals A₁-A₄, n, W, Q, R¹, R⁶,M¹, M² and Z¹-Z³ have the meanings given above.

According to the invention, “alkyl”—on its own or as part of a chemicalgroup—represents straight-chain or branched hydrocarbons preferablyhaving 1 to 6 carbon atoms such as, for example, methyl, ethyl,n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, pentyl,1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl,1,1-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl,1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,1,2-dimethylpropyl, 1,3-dimethylbutyl, 1,4-dimethylbutyl,2,3-dimethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl,3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl,1-ethylbutyl and 2-ethylbutyl. Preference is furthermore given to alkylgroups having 1 to 4 carbon atoms such as, inter alia, methyl, ethyl,n-propyl, isopropyl, n-butyl, isobutyl, s-butyl or t-butyl. The alkylgroups according to the invention may be substituted by one or moreidentical or different radicals.

According to the invention, “alkenyl”—on its own or as part of achemical group—represents straight-chain or branched hydrocarbonspreferably having 2 to 6 carbon atoms and at least one double bond suchas, for example, vinyl, 2-propenyl, 2-butenyl, 3-butenyl,1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl,4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl,1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl,1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl,2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl,2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl,3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl,2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl,1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-2-butenyl,1,2-dimethyl-3-butenyl, 1,3-dimethyl-2-butenyl, 2,2-dimethyl-3-butenyl,2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 1-ethyl-2-butenyl,1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl and1-ethyl-2-methyl-2-propenyl. Preference is furthermore given to alkenylgroups having 2 to 4 carbon atoms such as, inter alia, 2-propenyl,2-butenyl or 1-methyl-2-propenyl. The alkenyl groups according to theinvention may be substituted by one or more identical or differentradicals.

According to the invention, “alkynyl”—on its own or as part of achemical group—represents straight-chain or branched hydrocarbonspreferably having 2 to 6 carbon atoms and at least one triple bond suchas, for example, 2-propynyl, 2-butyryl, 3-butyryl, 1-methyl-2-propynyl,2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-3-butyryl,2-methyl-3-butyryl, 1-methyl-2-butyryl, 1,1-dimethyl-2-propynyl,1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl,1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl,2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl,4-methyl-2-pentynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl,2,2-dimethyl-3-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butyryl,1-ethyl-1-methyl-2-propynyl and 2,5-hexadiynyl. Preference isfurthermore given to alkynyl groups having 2 to 4 carbon atoms such as,inter alia, ethynyl, 2-propynyl or 2-butynyl-2-propenyl. The alkynylgroups according to the invention may be substituted by one or moreidentical or different radicals.

According to the invention, “cycloalkyl”—on its own or as part of achemical group—represents mono-, bi- or tricyclic hydrocarbonspreferably having 3 to 10 carbons such as, for example, cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl,bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl or adamantyl. Preference isfurthermore given to cycloalkyl groups having 3, 4, 5, 6 or 7 carbonatoms such as, inter alia, cyclopropyl or cyclobutyl. The cycloalkylgroups according to the invention may be substituted by one or moreidentical or different radicals.

According to the invention, “alkylcycloalkyl” represents mono-, bi- ortricyclic alkylcycloalkyl preferably having 4 to 10 or 4 to 7 carbonatoms such as, for example, ethylcyclopropyl, isopropylcyclobutyl,3-methylcyclopentyl and 4-methylcyclohexyl. Preference is furthermoregiven to alkylcycloalkyl groups having 4, 5 or 7 carbon atoms such as,inter alia, ethylcyclopropyl or 4-methylcyclohexyl. The alkylcycloalkylgroups according to the invention may be substituted by one or moreidentical or different radicals.

According to the invention, “cycloalkylalkyl” represents mono-, bi- ortricyclic cycloalkylalkyl preferably having 4 to 10 or 4 to 7 carbonatoms such as, for example, cyclopropylmethyl, cyclobutylmethyl,cyclopentylmethyl, cyclohexylmethyl and cyclopentylethyl. Preference isfurthermore given to cycloalkylalkyl groups having 4, 5 or 7 carbonatoms such as, inter alia, cyclopropylmethyl or cyclobutylmethyl. Thecycloalkylalkyl groups according to the invention may be substituted byone or more identical or different radicals.

According to the invention, “halogen” represents fluorine, chlorine,bromine or iodine, in particular fluorine, chlorine or bromine.

The halogen-substituted chemical groups according to the invention suchas, for example, haloalkyl, halocycloalkyl, haloalkoxy,haloalkylsulphanyl, haloalkylsulphinyl or haloalkylsulphonyl are mono-or polysubstituted by halogen up to the maximum possible number ofsubstituents. In the case of polysubstitution by halogen, the halogenatoms can be identical or different, and can all be attached to one orto a plurality of carbon atoms. Here, halogen represents in particularfluorine, chlorine, bromine or iodine, preferably fluorine, chlorine orbromine and particularly preferably fluorine.

According to the invention, “halocycloalkyl” represents mono-, bi- ortricyclic halocycloalkyl having preferably 3 to 10 carbon atoms such as,inter alia, 1-fluorocyclopropyl, 2-fluorocyclopropyl or1-fluorocyclobutyl. Preference is furthermore given to halocycloalkylhaving 3, 5 or 7 carbon atoms. The halocycloalkyl groups according tothe invention may be substituted by one or more identical or differentradicals.

According to the invention, “haloalkyl”, “haloalkenyl” or “haloalkynyl”represents halogen-substituted alkyl, alkenyl or alkynyl groups havingpreferably 1 to 9 identical or different halogen atoms such as, forexample, monohaloalkyl such as CH₂CH₂Cl, CH₂CH₂F, CHClCH₃, CHFCH₃,CH₂Cl, CH₂F; perhaloalkyl such as CCl₃ or CF₃ or CF₂CF₃; polyhaloalkylsuch as CHF₂, CH₂F, CH₂CHFCl, CHCl₂, CF₂CF₂H, CH₂CF₃. This appliescorrespondingly to haloalkenyl and other halogen-substituted radicals.Haloalkoxy is, for example, OCF₃, OCHF₂, OCH₂F, OCF₂CF₃, OCH₂CF₃ andOCH₂CH₂Cl.

Further examples for haloalkyl groups are trichloromethyl,chlorodifluoromethyl, dichlorofluoromethyl, chloromethyl, bromomethyl,1-fluoroethyl, 2fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2,2,2-trichloroethyl, 2-chloro-2,2-difluoroethyl, pentafluoroethyl andpentafluoro-t-butyl. Preference is given to haloalkyl groups having 1 to4 carbon atoms and 1 to 9, preferably 1 to 5, identical or differenthalogen atoms selected from fluorine, chlorine and bromine. Particularpreference is given to haloalkyl groups having 1 or 2 carbon atoms and 1to 5 identical or different halogen atoms selected from fluorine andchlorine such as, inter alia, difluoromethyl, trifluoromethyl or2,2-difluoroethyl.

According to the invention, “hydroxyalkyl” represents a straight-chainor branched alcohol preferably having 1 to 6 carbon atoms such as, forexample, methanol, ethanol, n-propanol, isopropanol, n-butanol,isobutanol, s-butanol and t-butanol. Preference is furthermore given tohydroxyalkyl groups having 1 to 4 carbon atoms. The hydroxyalkyl groupsaccording to the invention may be substituted by one or more identicalor different radicals.

According to the invention, “alkoxy” represents a straight-chain orbranched O-alkyl preferably having 1 to 6 carbon atoms such as, forexample, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy,s-butoxy and t-butoxy. Preference is furthermore given to alkoxy groupshaving 1 to 4 carbon atoms. The alkoxy groups according to the inventionmay be substituted by one or more identical or different radicals.

According to the invention, “haloalkoxy” represents halogen-substitutedstraight-chain or branched O-alkyl preferably having 1 to 6 carbon atomssuch as, inter alia, difluoromethoxy, trifluoromethoxy,2,2-difluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2,2,2-trifluoroethoxy and2-chloro-1,1,2-trifluoroethoxy. Preference is furthermore given tohaloalkoxy groups having 1 to 4 carbon atoms. The haloalkoxy groupsaccording to the invention may be substituted by one or more identicalor different radicals.

According to the invention, “alkylsulphanyl” represents straight-chainor branched S-alkyl preferably having 1 to 6 carbon atoms such as, forexample, methylthio, ethylthio, n-propylthio, isopropylthio,n-butylthio, isobutylthio, s-butylthio and t-butylthio. Preference isfurthermore given to alkylsulphanyl groups having 1 to 4 carbon atoms.The alkylsulphanyl groups according to the invention may be substitutedby one or more identical or different radicals.

Examples of haloalkylsulphanylalkyl groups, i.e. halogen-substitutedalkylsulphanyl groups, are inter alia difluoromethylthio,trifluoromethylthio, trichloromethylthio, chlorodifluoromethylthio,1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio,1,1,2,2-tetrafluoroethylthio, 2,2,2-trifluoroethylthio or2-chloro-1,1,2-trifluoroethylthio.

According to the invention, “alkylsulphinyl” represents straight-chainor branched alkylsulphinyl preferably having 1 to 6 carbon atoms suchas, for example, methylsulphinyl, ethylsulphinyl, n-propylsulphinyl,isopropylsulphinyl, n-butylsulphinyl, isobutylsulphinyl,s-butylsulphinyl and t-butylsulphinyl. Preference is furthermore givento alkylsulphinyl groups having 1 to 4 carbon atoms. The alkylsulphinylgroups according to the invention may be substituted by one or moreidentical or different radicals.

Examples of haloalkylsulphinyl groups, i.e. halogen-substitutedalkylsulphinyl groups, are inter alia difluoromethylsulphinyl,trifluoromethylsulphinyl, trichloromethylsulphinyl,chlorodifluoromethylsulphinyl, 1-fluoroethylsulphinyl,2-fluoroethylsulphinyl, 2,2-difluoroethylsulphinyl,1,1,2,2-tetrafluoroethylsulphinyl, 2,2,2-trifluoroethylsulphinyl and2-chloro-1,1,2-trifluoroethylsulphinyl.

According to the invention, “alkylsulphonyl” represents straight-chainor branched alkylsulphonyl preferably having 1 to 6 carbon atoms suchas, for example, methylsulphonyl, ethylsulphonyl, n-propylsulphonyl,isopropylsulphonyl, n-butylsulphonyl, isobutylsulphonyl,s-butylsulphonyl and t-butylsulphonyl. Preference is furthermore givento alkylsulphonyl groups having 1 to 4 carbon atoms. The alkylsulphonylgroups according to the invention may be substituted by one or moreidentical or different radicals.

Examples of haloalkylsulphonyl groups, i.e. halogen-substitutedalkylsulphonyl groups, are inter alia difluoromethylsulphonyl,trifluoromethylsulphonyl, trichloromethylsulphonyl,chlorodifluoromethylsulphonyl, 1-fluoroethylsulphonyl,2-fluoroethylsulphonyl, 2,2-difluoroethylsulphonyl,1,1,2,2-tetrafluoroethylsulphonyl, 2,2,2-trifluoroethylsulphonyl and2-chloro-1,1,2-trifluoroethylsulphonyl.

According to the invention, “alkylcarbonyl” represents straight-chain orbranched alkyl-C(═O) preferably having 2 to 7 carbon atoms such asmethylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl,s-butylcarbonyl and t-butylcarbonyl. Preference is furthermore given toalkylcarbonyl groups having 1 to 4 carbon atoms. The alkylcarbonylgroups according to the invention may be substituted by one or moreidentical or different radicals.

According to the invention, “cycloalkylcarbonyl” representsstraight-chain or branched cycloalkylcarbonyl preferably having 3 to 10carbon atoms in the cycloalkyl moiety such as, for example,cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl,cyclohexylcarbonyl, cycloheptylcarbonyl, cyclooctylcarbonyl,bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octylcarbonyl and adamantylcarbonyl.Preference is furthermore given to cycloalkylcarbonyl having 3, 5 or 7carbon atoms in the cycloalkyl moiety. The cycloalkylcarbonyl groupsaccording to the invention may be substituted by one or more identicalor different radicals.

According to the invention, “alkoxycarbonyl”—alone or as a constituentof a chemical group—represents straight-chain or branchedalkoxycarbonyl, preferably having 1 to 6 carbon atoms or having 1 to 4carbon atoms in the alkoxy moiety such as, for example, methoxycarbonyl,ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, s-butoxycarbonyland t-butoxycarbonyl. The alkoxycarbonyl groups according to theinvention may be substituted by one or more identical or differentradicals.

According to the invention, “alkylaminocarbonyl” representsstraight-chain or branched alkylaminocarbonyl having preferably 1 to 6carbon atoms or 1 to 4 carbon atoms in the alkyl moiety, such as, forexample, methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl,isopropylaminocarbonyl, s-butylaminocarbonyl and t-butylaminocarbonyl.The alkylaminocarbonyl groups according to the invention may besubstituted by one or more identical or different radicals.

According to the invention, “N,N-dialkylaminocarbonyl” representsstraight-chain or branched N,N-dialkylaminocarbonyl having preferably 1to 6 carbon atoms or 1 to 4 carbon atoms in the alkyl moiety, such as,for example, N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl,N,N-di(n-propylamino)carbonyl, N,N-di(isopropylamino)carbonyl andN,N-di-(s-butylamino)carbonyl. The N,N-dialkylaminocarbonyl groupsaccording to the invention may be substituted by one or more identicalor different radicals.

According to the invention, “aryl” represents a mono-, bi- or polycyclicaromatic system having preferably 6 to 14, in particular 6 to 10 ringcarbon atoms such as, for example, phenyl, naphthyl, anthryl,phenanthrenyl, preferably phenyl. Furthermore, aryl also representspolycyclic systems such as tetrahydronaphthyl, indenyl, indanyl,fluorenyl, biphenyl, where the bonding site is on the aromatic system.The aryl groups according to the invention may be substituted by one ormore identical or different radicals.

Examples for substituted aryl groups are the arylalkyl groups which maylikewise be substituted by one or more identical or different radicalsin the alkyl and/or aryl moiety. Examples for such arylalkyl groups areinter alia benzyl and 1-phenylethyl.

According to the invention, “heterocycle”, “heterocyclic ring” or“heterocyclic ring system” represents a carbocyclic ring system havingat least one ring in which at least one carbon atom is replaced by aheteroatom, preferably by a heteroatom from the group consisting of N,O, S, P, B, Si, Se, and which is saturated, unsaturated orheteroaromatic and may be unsubstituted or substituted by a substituentZ, where the point of attachment is located at a ring atom. Unlessdefined differently, the heterocyclic ring contains preferably 3 to 9ring atoms, especially 3 to 6 ring atoms, and one or more, preferably 1to 4, in particular 1, 2 or 3, heteroatoms in the heterocyclic ring,preferably from the group consisting of N, O, and S, although no twooxygen atoms should be directly adjacent. The heterocyclic rings usuallycontain not more than 4 nitrogen atoms and/or not more than 2 oxygenatoms and/or not more than 2 sulphur atoms. If the heterocyclyl radicalor the heterocyclic ring is optionally substituted, it can be fused toother carbocyclic or heterocyclic rings. In the case of optionallysubstituted heterocyclyl, the invention also embraces polycyclic systemssuch as, for example, 8-azabicyclo[3.2.1]octanyl or1-azabicyclo[2.2.1]heptyl. In the case of optionally substitutedheterocyclyl, the invention also embraces spirocyclic systems such as,for example, 1-oxa-5-azaspiro[2.3]hexyl.

Heterocyclyl groups according to the invention are, for example,piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, dihydropyranyl,tetrahydropyranyl, dioxanyl, pyrrolinyl, pyrrolidinyl, imidazolinyl,imidazolidinyl, thiazolidinyl, oxazolidinyl, dioxolanyl, dioxolyl,pyrazolidinyl, tetrahydrofuranyl, dihydrofuranyl, oxetanyl, oxiranyl,azetidinyl, aziridinyl, oxazetidinyl, oxaziridinyl, oxazepanyl,oxazinanyl, azepanyl, oxopyrrolidinyl, dioxopyrrolidinyl,oxomorpholinyl, oxopiperazinyl and oxepanyl.

Heteroarylene, i.e. heteroaromatic systems, has a particular meaning.According to the invention, the term heteroaryl representsheteroaromatic compounds, i.e. completely unsaturated aromaticheterocyclic compounds which fall under the above definition ofheterocycles. Preference is given to 5- to 7-membered rings having 1 to3, preferably 1 or 2, identical or different heteroatoms from the groupabove. Heteroaryl groups according to the invention are, for example,furyl, thienyl, pyrazolyl, imidazolyl, 1,2,3- and 1,2,4-triazolyl,isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-, 1,3,4-, 1,2,4- and1,2,5-oxadiazolyl, azepinyl, pyrrolyl, pyridyl, pyridazinyl,pyrimidinyl, pyrazinyl, 1,3,5-, 1,2,4- and 1,2,3-triazinyl, 1,2,4-,1,3,2-, 1,3,6- and 1,2,6-oxazinyl, oxepinyl, thiepinyl,1,2,4-triazolonyl and 1,2,4-diazepinyl. The heteroaryl groups accordingto the invention may also be substituted by one or more identical ordifferent radicals.

Substituted groups such as a substituted alkyl, alkenyl, alkynyl,cycloalkyl, aryl, phenyl, benzyl, heterocyclyl and heteroaryl radicalare, for example, a substituted radical derived from the unsubstitutedbase structure, where the substituents are, for example, one or more,preferably 1, 2 or 3, radicals from the group of halogen, alkoxy,alkylsulphanyl, hydroxyl, amino, nitro, carboxyl or a group equivalentto the carboxyl group, cyano, isocyano, azido, alkoxycarbonyl,alkylcarbonyl, formyl, carbamoyl, mono- and N,N-dialkylaminocarbonyl,substituted amino such as acylamino, mono- and N,N-dialkylamino,trialkylsilyl and optionally substituted cycloalkyl, optionallysubstituted aryl, optionally substituted heterocyclyl, where each of thelatter cyclic groups may also be bonded via heteroatoms or divalentfunctional groups such as in the alkyl radicals mentioned, andalkylsulphinyl, including both enantiomers of the alkylsulphonyl group,alkylsulphonyl, alkylphosphinyl, alkylphosphonyl and, in the case ofcyclic radicals (=“cyclic skeleton”), also alkyl, haloalkyl,alkylsulphanylalkyl, alkoxyalkyl, optionally substituted mono- andN,N-dialkylaminoalkyl and hydroxyalkyl.

The term “substituted groups”, such as substituted alkyl etc., includes,as substituents, in addition to the saturated hydrocarbonaceous radicalsmentioned, corresponding unsaturated aliphatic and aromatic radicalssuch as optionally substituted alkenyl, alkynyl, alkenyloxy, alkynyloxy,alkenylthio, alkynylthio, alkenyloxycarbonyl, alkynyloxycarbonyl,alkenylcarbonyl, alkynylcarbonyl, mono- and N,N-dialkenylaminocarbonyl,mono- and dialkynylaminocarbonyl, mono- and N,N-dialkenylamino, mono-and N,N-dialkynylamino, trialkenylsilyl, trialkynylsilyl, optionallysubstituted cycloalkenyl, optionally substituted cycloalkynyl, phenyl,phenoxy etc. In the case of substituted cyclic radicals with aliphaticcomponents in the ring, cyclic systems with those substituents bonded tothe ring by a double bond are also included, for example those having analkylidene group such as methylidene or ethylidene, or an oxo group,imino group or substituted imino group.

When two or more radicals form one or more rings, these may becarbocyclic, heterocyclic, saturated, partly saturated, unsaturated, forexample also aromatic and further substituted.

The substituents mentioned by way of example (“first substituent level”)may, if they contain hydrocarbon-containing moieties, optionally befurther substituted therein (“second substituent level”), for example byone of the substituents as defined for the first substituent level.Corresponding further substituent levels are possible. The term“substituted radical” preferably embraces just one or two substituentlevels.

Preferred substituents for the substituent levels are, for example,amino, hydroxy, halogen, nitro, cyano, isocyano, mercapto,isothiocyanato, carboxyl, carboxamide, SF₅, aminosulphonyl, alkyl,cycloalkyl, alkenyl, cycloalkenyl, alkynyl, N-monoalkylamino,N,N-dialkylamino, N-alkanoylamino, alkoxy, alkenyloxy, alkynyloxy,cycloalkoxy, cycloalkenyloxy, alkoxycarbonyl, alkenyloxycarbonyl,alkynyloxycarbonyl, aryloxycarbonyl, alkanoyl, alkenylcarbonyl,alkynylcarbonyl, arylcarbonyl, alkylsulphanyl, cycloalkylsulphanyl,alkenylthio, cycloalkenylthio, alkynylthio, alkylsulphenyl andalkylsulphinyl, where both enantiomers of the alkylsulphinyl group areincluded, alkylsulphonyl, N-monoalkylaminosulphonyl,N,N-dialkylaminosulphonyl, alkylphosphinyl, alkylphosphonyl, where inthe case of alkylphosphinyl and alkylphosphonyl both enantiomers areincluded, N-alkylaminocarbonyl, N,N-dialkylaminocarbonyl,N-alkanoylaminocarbonyl, N-alkanoyl-N-alkylaminocarbonyl, aryl, aryloxy,benzyl, benzyloxy, benzylthio, arylthio, arylamino, benzylamino,heterocyclyl and trialkylsilyl.

Substituents composed of a plurality of substituent levels arepreferably alkoxyalkyl, alkylsulphanylalkyl, alkylsulphanylalkoxy,alkoxyalkoxy, phenethyl, benzyloxy, haloalkyl, halocycloalkyl,haloalkoxy, haloalkylsulphanyl, haloalkylsulphinyl, haloalkylsulphonyl,haloalkanoyl, haloalkylcarbonyl, haloalkoxycarbonyl, haloalkoxyalkoxy,haloalkoxyalkylsulphanyl, haloalkoxyalkanoyl, haloalkoxyalkyl.

In the case of radicals having carbon atoms, preference is given tothose having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms,especially 1 or 2 carbon atoms. Preference is generally given tosubstituents from the group of halogen, e.g. fluorine and chlorine,(C₁-C₄)-alkyl, preferably methyl or ethyl, (C₁-C₄)-haloalkyl, preferablytrifluoromethyl, (C₁-C₄)-alkoxy, preferably methoxy or ethoxy,(C₁-C₄)-haloalkoxy, nitro and cyano. Particular preference is given hereto the substituents methyl, methoxy, fluorine and chlorine.

Substituted amino such as mono- or disubstituted amino means a radicalfrom the group of the substituted amino radicals which areN-substituted, for example, by one or two identical or differentradicals from the group consisting of alkyl, hydroxy, amino, alkoxy,acyl and aryl; preferably N-mono- and N,N-dialkylamino, (for examplemethylamino, ethylamino, N,N-dimethylamino, N,N-diethylamino,N,N-di-n-propylamino, N,N-diisopropylamino or N,N-dibutylamino), N-mono-or N,N-dialkoxyalkylamino groups (for example N-methoxymethylamino,N-methoxyethylamino, N,N-di(methoxymethyl)amino orN,N-di(methoxyethyl)amino), N-mono- and N,N-diarylamino, such asoptionally substituted anilines, acylamino, N,N-diacylamino,N-alkyl-N-arylamino, N-alkyl-N-acylamino and also saturatedN-heterocycles; preference is given here to alkyl radicals having 1 to 4carbon atoms; here, aryl is preferably phenyl or substituted phenyl; foracyl, the definition given further below applies, preferably(C₁-C₄)-alkanoyl. The same applies to substituted hydroxylamino orhydrazino.

According to the invention, the term “cyclic amino groups” embracesheteroaromatic or aliphatic ring systems having one or more nitrogenatoms. The heterocycles are saturated or unsaturated, consist of one ormore optionally fused ring systems and optionally contain furtherheteroatoms such as, for example, one or two nitrogen, oxygen and/orsulphur atoms. Furthermore, the term also includes groups having a spiroring or a bridged ring system. The number of atoms which form the cyclicamino group is not limited and, in the case of a one-ring system, forexample, the groups can consist of 3 to 8 ring atoms, and in the case ofa two-ring system of 7 to 11 atoms.

Examples of cyclic amino groups having saturated and unsaturatedmonocyclic groups having a nitrogen atom as heteroatom which may bementioned are 1-azetidinyl, pyrrolidino, 2-pyrrolidin-1-yl, 1-pyrrolyl,piperidino, 1,4-dihydropyrazin-1-yl, 1,2,5,6-tetrahydropyrazin-1-yl,1,4-dihydropyridin-1-yl, 1,2,5,6-tetrahydropyridin-1-yl,homopiperidinyl; examples of cyclic amino groups having saturated andunsaturated monocyclic groups having two or more nitrogen atoms asheteroatoms which may be mentioned are 1-imidazolidinyl, 1-imidazolyl,1-pyrazolyl, 1-triazolyl, 1-tetrazolyl, 1-piperazinyl,1-homopiperazinyl, 1,2-dihydropiperazin-1-yl, 1,2-dihydropyrimidin-1-yl,perhydropyrimidin-1-yl, 1,4-diazacycloheptan-1-yl; examples of cyclicamino groups having saturated and unsaturated monocyclic groups havingone or two oxygen atoms and one to three nitrogen atoms as heteroatoms,such as, for example, oxazolidin-3-yl, 2,3-dihydroisoxazol-2-yl,isoxazol-2-yl, 1,2,3-oxadiazin-2-yl, morpholino, examples of cyclicamino groups having saturated and unsaturated monocyclic groups havingone to three nitrogen atoms and one to two sulphur atoms as heteroatomswhich may be mentioned are thiazolidin-3-yl, isothiazolin-2-yl,thiomorpholino, or dioxothiomorpholino; examples of cyclic amino groupshaving saturated and unsaturated fused cyclic groups which may bementioned are indol-1-yl, 1,2-dihydrobenzimidazol-1-yl,perhydropyrrolo[1,2-a]pyrazin-2-yl; examples of cyclic amino groupshaving spirocyclic groups which may be mentioned are2-azaspiro[4,5]decan-2-yl; examples of cyclic amino groups havingbridged heterocyclic groups which may be mentioned are2-azabicyclo[2.2.1]heptan-7-yl.

Substituted amino also includes quaternary ammonium compounds (salts)with four organic substituents on the nitrogen atom.

Optionally substituted phenyl is preferably phenyl which isunsubstituted or mono- or polysubstituted, preferably up totrisubstituted, by identical or different radicals from the group ofhalogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy,(C₁-C₄)-alkylsulphanyl, (C₁-C₄)-haloalkylsulphanyl, cyano, isocyano andnitro, for example o-, m- and p-tolyl, dimethylphenyls, 2-, 3- and4-chlorophenyl, 2-, 3- and 4-fluorophenyl, 2-, 3- and 4-trifluoromethyl-and -trichloromethylphenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-,m- and p-methoxyphenyl.

Optionally substituted cycloalkyl is preferably cycloalkyl, which isunsubstituted or mono- or polysubstituted, preferably up totrisubstituted, by identical or different radicals from the group ofhalogen, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl and (C₁-C₄)-haloalkoxy, especially by one or two(C₁-C₄)-alkyl radicals.

Optionally substituted heterocyclyl is preferably heterocyclyl which isunsubstituted or mono- or polysubstituted, preferably up totrisubstituted, by identical or different radicals from the group ofhalogen, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy, nitro and oxo, especially mono-or polysubstituted by radicals from the group of halogen, (C₁-C₄)-alkyl,(C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl and oxo, most preferably substitutedby one or two (C₁-C₄)-alkyl radicals.

Examples of alkyl-substituted heteroaryl groups are furylmethyl,thienylmethyl, pyrazolylmethyl, imidazolylmethyl, 1,2,3- and1,2,4-triazolylmethyl, isoxazolylmethyl, thiazolylmethyl,isothiazolylmethyl, 1,2,3-, 1,3,4-, 1,2,4- and 1,2,5-oxadiazolylmethyl,azepinylmethyl, pyrrolylmethyl, pyridylmethyl, pyridazinylmethyl,pyrimidinylmethyl, pyrazinylmethyl, 1,3,5-, 1,2,4- and1,2,3-triazinylmethyl, 1,2,4-, 1,3,2-, 1,3,6- and 1,2,6-oxazinylmethyl,oxepinylmethyl, thiepinylmethyl and 1,2,4-diazepinylmethyl.

Salts which are suitable according to the invention of the compoundsaccording to the invention, for example salts with bases or acidaddition salts, are all customary non-toxic salts, preferablyagriculturally and/or physiologically acceptable salts. For examplesalts with bases or acid addition salts. Preference is given to saltswith inorganic bases such as, for example, alkali metal salts (e.g.sodium, potassium or caesium salts), alkaline earth metal salts (e.g.calcium or magnesium salts), ammonium salts or salts with organic bases,in particular with organic amines, such as, for example,triethylammonium, dicyclohexylammonium, N,N′-dibenzylethylenediammonium,pyridinium, picolinium or ethanolammonium salts, salts with inorganicacids (e.g. hydrochlorides, hydrobromides, dihydrosulphates,trihydrosulphates or phosphates), salts with organic carboxylic acids ororganic sulphoacids (e.g. formates, acetates, trifluoroacetates,maleates, tartrates, methanesulphonates, benzenesulphonates or4-toluenesulphonates). It is known that t-amines such as some of thecompounds according to the invention are capable of forming N-oxides,which also represent salts according to the invention.

The compounds according to the invention may, depending on the nature ofthe substituents, be in the form of geometric and/or optically activeisomers or corresponding isomer mixtures in different compositions.These stereoisomers are, for example, enantiomers, diastereomers,atropisomers or geometric isomers. Accordingly, the inventionencompasses both pure stereoisomers and any mixtures of these isomers.

If appropriate, the compounds according to the invention may be presentin various polymorphic forms or as a mixture of different polymorphicforms. Both the pure polymorphs and the polymorph mixtures are providedby the invention and can be used in accordance with the invention.

The compounds of the general formula (I) can be mixed or applied jointlywith other insecticidal, nematicidal, acaricidal or antimicrobial activecompounds. In these mixtures or joint applications, synergistic effectsoccur, i.e. the observed effect of these mixture or joint applicationsis higher than the total of the effects of the individual activecompounds in these applications. Examples of such mixing or combinationpartners are:

(1) Acetylcholinesterase (AChE) inhibitors such as, for example,carbamates, for example alanycarb, aldicarb, bendiocarb, benfuracarb,butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan,ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb,methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur,thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb; ororganophosphates, for example acephate, azamethiphos, azinphos-ethyl,azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos,chlormephos, chloropyrifos, chloropyrifos-methyl, coumaphos, cyanophos,demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate,dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur,fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos,isofenphos, isopropyl O-(methoxyaminothiophosphoryl)salicylate,isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos,monocrotophos, naled, omethoate, oxydemeton-methyl, parathion,parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon,phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos,pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos,temephos, terbufos, tetrachlorvinphos, thiometon, triazophos,trichlorfon and vamidothion.(2) GABA-gated chloride channel antagonists such as, for example,cyclodiene organochlorines, e.g. chlordane and endosulfan; orphenylpyrazoles (fiproles), e.g. ethiprole and fipronil.(3) Sodium channel modulators/voltage-dependent sodium channel blockerssuch as, for example,pyrethroids, e.g. acrinathrin, allethrin, d-cis-trans allethrin, d-transallethrin, bifenthrin, bioallethrin, bioallethrin s-cyclopentenylisomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin,cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin,alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin,zeta-cypermethrin, cyphenothrin [(1R)-trans-isomers], deltamethrin,empenthrin [(EZ)-(1R)-isomers], esfenvalerate, etofenprox,fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate,halfenprox, imiprothrin, kadethrin, permethrin, phenothrin[(1R)-trans-isomer], prallethrin, pyrethrins (pyrethrum), resmethrin,silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomers)],tralomethrin and transfluthrin; orDDT; or methoxychlor.(4) Nicotinergic acetylcholine receptor (nAChR) agonists such as, forexample, neonicotinoids, e.g. acetamiprid, clothianidin, dinotefuran,imidacloprid, nitenpyram, thiacloprid and thiamethoxam; ornicotine; orsulfoxaflor.(5) Nicotinergic acetylcholine receptor (nAChR) allosteric activatorssuch as, for example,spinosyns, e.g. spinetoram and spinosad.(6) Chloride channel activators such as, for example,avermectins/milbemycins, for example abamectin, emamectin benzoate,lepimectin and milbemectin.(7) Juvenile hormone imitators such as, for example,juvenile hormone analogues, e.g. hydroprene, kinoprene and methoprene;orfenoxycarb; or pyriproxyfen.(8) Active compounds with unknown or nonspecific mechanisms of actionsuch as, for example,alkyl halides, e.g. methyl bromide and other alkyl halides; orchloropicrin; or sulphuryl fluoride; or borax; or tartar emetic.(9) Selective antifeedants, for example pymetrozine or flonicamid.(10) Mite growth inhibitors, for example clofentezine, hexythiazox anddiflovidazin; or etoxazole.(11) Microbial disruptors of the insect gut membrane, e.g. Bacillusthuringiensis subspecies israelensis, Bacillus thuringiensis subspeciesaizawai, Bacillus thuringiensis subspecies kurstaki, Bacillusthuringiensis subspecies tenebrionis and B.t. plant proteins: Cry1Ab,Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1/35Ab1; orBacillus sphaericus.(12) Oxidative phosphorylation inhibitors, ATP disruptors, for examplediafenthiuron; ororganotin compounds, e.g. azocyclotin, cyhexatin and fenbutatin oxide;orpropargite; or tetradifon.(13) Oxidative phosphorylation decouplers acting by interrupting the Hproton gradient such as, for example, chlorfenapyr, DNOC andsulfluramid.(14) Nicotinergic acetylcholine receptor antagonists such as, forexample, bensultap, cartap hydrochloride, thiocyclam, andthiosultap-sodium.(15) Chitin biosynthesis inhibitors, type 0, such as, for example,bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron,flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron,teflubenzuron and triflumuron.(16) chitin biosynthesis inhibitors, type 1, such as, for example,buprofezin.(17) Molting disruptors, dipteran such as, for example, cyromazine.(18) Ecdysone receptor agonists such as, for example, chromafenozide,halofenozide, methoxyfenozide and tebufenozide.(19) Octopaminergic agonists such as, for example, amitraz.(20) Complex-III electron transport inhibitors such as, for example,hydramethylnone or acequinocyl or fluacrypyrim.(21) Complex-I electron transport inhibitors, for exampleMETI acaricides, e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben,tebufenpyrad and tolfenpyrad; orrotenone (Derris).(22) Voltage-gated sodium channel blockers, for example indoxacarb ormetaflumizone.(23) Inhibitors of acetyl-CoA carboxylase such as, for example, tetronicand tetramic acid derivatives, e.g. spirodiclofen, spiromesifen andspirotetramat.(24) Complex-IV electron transport inhibitors such as, for example,phosphines, e.g. aluminium phosphide, calcium phosphide, phosphine andzinc phosphide; or cyanide.(25) Complex-II electron transport inhibitors, such as, for example,cyenopyrafen and cyflumetofen.(28) Ryanodine receptor effectors such as, for example,diamides, e.g. chlorantraniliprole, cyantraniliprole and flubendiamide.

Further active compounds having an unknown mechanism of action, such as,for example, amidoflumet, azadirachtin, benclothiaz, benzoximate,bifenazate, bromopropylate, chinomethionat, cryolite, dicofol,diflovidazin, fluensulphone, flufenerim, flufiprole, fluopyram,fufenozide, imidaclothiz, iprodione, meperfluthrin, pyridalyl,pyrifluquinazon, tetramethylfluthrin and iodomethane; and additionallypreparations based on Bacillus firmus (particularly strain CNCM I-1582,for example VOTiVO™, BioNem), and the following known active compounds:

3-bromo-N-{2-bromo-4-chlor-6-[(1-cyclopropylethyl)carbamoyl]phenyl}-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide (known from WO 2005/077934),4-{[(6-bromopyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one(known from WO 2007/115644),4-{[(6-fluoropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-one(known from WO 2007/115644),4-{[(2-chloro-1,3-thiazol-5-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one(known from WO 2007/115644),4-{[(6-chloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one(known from WO 2007/115644), flupyradifurone,4-{[(6-chloro-5-fluoropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-one(known from WO 2007/115643),4-{[(5,6-dichloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one(known from WO 2007/115646),4-{[(6-chloro-5-fluoropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one(known from WO 2007/115643),4-{[(6-chloropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one (knownfrom EP A 0 539 588),4-{[(6-chloropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-one (known fromEP A 0 539 588),{[1-(6-chloropyridin-3-yl)ethyl](methyl)oxido-λ⁴-sulphanylidene}cyanamide(known from WO2007/149134) and its diastereomers{[(1R)-1-(6-chloropyridin-3-yl)ethyl](methyl)oxido-λ⁴-sulphanylidene}cyanamide(A) and{[(1S)-1-(6-chloropyridin-3-yl)ethyl](methyl)oxido-λ⁴-sulphanylidene}cyanamide(B) (likewise known from WO 2007/149134) and also diastereomers[(R)-methyl(oxido){(1R)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-λ⁴-sulphanylidene]cyanamide(A1) and [(S)-methyl(oxido){(1S)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-λ⁴-sulphanylidene]cyanamide(A2), identified as diastereomer group A (known from WO 2010/074747, WO2010/074751), [(R)-methyl(oxido){(1S)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-λ⁴-sulphanylidene]cyanamide(B1) and [(S)-methyl(oxido){(1R)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-λ⁴-sulphanylidene]cyanamide(B2), identified as diastereomer group B (likewise known from WO2010/074747, WO 2010/074751) and11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-11-en-10-one(known from WO 2006/089633),3-(4′-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one(known from WO 2008/067911),1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine(known from WO 2006/043635), afidopyropen (known from WO 2008/066153),2-cyano-3-(difluoromethoxy)-N,N-dimethylbenzolsulphonamide (known fromWO 2006/056433), 2-cyano-3-(difluoromethoxy)-N-methylbenzolsulphonamide(known from WO 2006/100288),2-cyano-3-(difluoromethoxy)-N-ethylbenzenesulphonamide (known from WO2005/035486),4-(difluoromethoxy)-N-ethyl-N-methyl-1,2-benzothiazol-3-amine-1,1-dioxide(known from WO 2007/057407),N-[1-(2,3-dimethylphenyl)-2-(3,5-dimethylphenyl)ethyl]-4,5-dihydro-1,3-thiazol-2-amine(known from WO 2008/104503),{1′-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indol-3,4′-piperidine]-1(2H)-yl}(2-chloropyridin-4-yl)methanone(known from WO 2003/106457),3-(2,5-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one(known from WO 2009/049851),3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylethyl carbonate (known from WO 2009/049851),4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine(known from WO 2004/099160),(2,2,3,3,4,4,5,5-octafluoropentyl)(3,3,3-trifluoropropyl)malononitrile(known from WO 2005/063094),(2,2,3,3,4,4,5,5-octafluoropentyl)(3,3,4,4,4-pentafluorobutyl)malononitrile(known from WO 2005/063094),8-[2-(cyclopropylmethoxy)-4-(trifluoromethyl)phenoxy]-3-[6-(trifluoromethyl)pyridazin-3-yl]-3-azabicyclo[3.2.1]octane(known from WO 2007/040280), flometoquin, PF1364 (CAS Reg. No.1204776-60-2) (known from JP 2010/018586),5-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(1H-1,2,4-triazol-1-yl)benzonitrile(known from WO 2007/075459),5-[5-(2-chloropyridin-4-yl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(1H-1,2,4-triazol-1-yl)benzonitrile(known from WO 2007/075459),4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-{2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl}benzamide(known from WO 2005/085216),4-{[(6-chloropyridin-3-yl)methyl](cyclopropyl)amino}-1,3-oxazol-2(5H)-one,4-{[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino}-1,3-oxazol-2(5H)-one,4-{[(6-chloropyridin-3-yl)methyl](ethyl)amino}-1,3-oxazol-2(5H)-one,4-{[(6-chloropyridin-3-yl)methyl](methyl)amino}-1,3-oxazol-2(5H)-one(all known from WO 2010/005692), pyflubumide (known from WO2002/096882), methyl2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-chloro-3-methylbenzoyl]-2-methylhydrazinecarboxylate(known from WO 2005/085216), methyl2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-ethylhydrazinecarboxylate(known from WO 2005/085216), methyl2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-methylhydrazinecarboxylate(known from WO 2005/085216), methyl2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1,2-diethylhydrazinecarboxylate(known from WO 2005/085216), methyl2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-2-ethylhydrazinecarboxylate(known from WO 2005/085216),(5RS,7RS;5RS,7SR)-1-(6-chloro-3-pyridylmethyl)-1,2,3,5,6,7-hexahydro-7-methyl-8-nitro-5-propoxyimidazo[1,2-a]pyridine(known from WO 2007/101369),2-{6-[2-(5-fluoropyridin-3-yl)-1,3-thiazol-5-yl]pyridin-2-yl}pyrimidine(known from WO 2010/006713),2-{6-[2-(pyridin-3-yl)-1,3-thiazol-5-yl]pyridin-2-yl}pyrimidine (knownfrom WO 2010/006713),1-(3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-3-{[5-(trifluoromethyl)-1H-tetrazol-1-yl]methyl}-1H-pyrazole-5-carboxamide(known from WO 2010/069502),1-(3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-3-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl}-1H-pyrazole-5-carboxamide(known from WO 2010/069502),N-[2-(tert-butylcarbamoyl)-4-cyano-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-{[5-(trifluoromethyl)-1H-tetrazol-1-yl]methyl}-1H-pyrazole-5-carboxamide(known from WO 2010/069502),N-[2-(tert-butylcarbamoyl)-4-cyano-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl}-1H-pyrazole-5-carboxamide (known from WO 2010/069502),(1E)-N-[(6-chloropyridin-3-yl)methyl]-N′-cyano-N-(2,2-difluoroethyl)ethanimideamide(known from WO 2008/009360),N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide (known from CN 102057925), methyl2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-2-ethyl-1-methylhydrazinecarboxylate(known from WO 2011/049233), heptafluthrin, pyriminostrobin,flufenoxystrobin and3-chloro-N²-(2-cyanopropan-2-yl)-N¹-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-methylphenyl]phthalamide(known from WO2012/034472).

Antimicrobially Active Compounds:

(1) Ergosterol biosynthesis inhibitors, for example aldimorph,azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole,difenoconazole, diniconazole, diniconazole-M, dodemorph, dodemorphacetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole,fenhexamid, fenpropidin, fenpropimorph, fluquinconazole, flurprimidol,flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole,imazalil, imazalil sulphate, imibenconazole, ipconazole, metconazole,myclobutanil, naftifin, nuarimol, oxpoconazole, paclobutrazole,pefurazoate, penconazole, piperalin, prochloraz, propiconazole,prothioconazole, pyributicarb, pyrifenox, quinconazole, simeconazole,spiroxamine, tebuconazole, terbinafine, tetraconazole, triadimefon,triadimenol, tridemorph, triflumizole, triforine, triticonazole,uniconazole, uniconazole-p, viniconazole, voriconazole,1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol, methyl1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylate,N′-{5-(difluoromethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl-N-methylimidoformamide,N-ethyl-N-methyl-N′-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamideandO-[1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl]1H-imidazole-1-carbothioate.(2) Respiration inhibitors (respiratory chain inhibitors), for examplebixafen, boscalid, carboxin, diflumetorim, fenfuram, fluopyram,flutolanil, fluxapyroxad, furametpyr, furmecyclox, isopyrazam mixture ofthe syn-epimeric racemate 1RS,4SR,9RS and of the anti-epimeric racemate1RS,4SR,9SR, isopyrazam (anti-epimeric racemate), isopyrazam(anti-epimeric enantiomer 1R,4S,9S), isopyrazam (anti-epimericenantiomer 1S,4R,9R), isopyrazam (syn-epimeric racemate 1RS,4SR,9RS),isopyrazam (syn-epimeric enantiomer 1R,4S,9R), isopyrazam (syn-epimericenantiomer 1S,4R,9S), mepronil, oxycarboxin, penflufen, penthiopyrad,sedaxane, thifluzamide,1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,3-(difluoromethyl)-1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1H-pyrazole-4-carboxamide,3-(difluoromethyl)-N-[4-fluoro-2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-1H-pyrazole-4-carboxamideandN-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide.(3) Respiration inhibitors (respiratory chain inhibitors) acting oncomplex III of the respiratory chain, for example ametoctradin,amisulbrom, azoxystrobin, cyazofamid, dimoxystrobin, enestroburin,famoxadone, fenamidone, fluoxastrobin, kresoxim-methyl, metominostrobin,orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin,pyraoxystrobin, pyribencarb, trifloxystrobin,(2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylethanamide,(2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)ethanamide,(2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-(trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}ethanamide,(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylethenyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide,(2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide,2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridine-3-carboxamide,5-methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one,methyl(2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}sulphanyl)methyl]phenyl}-3-methoxyprop-2-enoate,N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-(formylamino)-2-hydroxybenzamide,2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamideand(2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide.(4) Mitosis and cell division inhibitors, for example benomyl,carbendazim, chlorfenazole, diethofencarb, ethaboxam, fluopicolide,fuberidazole, pencycuron, thiabendazole, thiophanate-methyl,thiophanate, zoxamide,5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidineand3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine.(5) Compounds with multisite activity, for example Bordeaux mixture,captafol, captan, chlorothalonil, copper formulations such as copperhydroxide, copper naphthenate, copper oxide, copper oxychloride, coppersulphate, dichlofluanid, dithianon, dodine, dodine free base, ferbam,fluorofolpet, folpet, guazatine, guazatine acetate, iminoctadine,iminoctadine albesilate, iminoctadine triacetate, mancopper, mancozeb,maneb, metiram, metiram zinc, oxine-copper, propamidine, propineb,sulphur and sulphur preparations, for example calcium polysulphide,thiram, tolylfluanid, zineb and ziram.(6) Resistance inductors, for example acibenzolar-S-methyl, isotianil,probenazole and tiadinil.(7) Amino acid and protein biosynthesis inhibitors, for exampleandoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycinhydrochloride hydrate, mepanipyrim and pyrimethanil.(8) ATP production inhibitors, for example fentin acetate, fentinchloride, fentin hydroxide and silthiofam.(9) Cell wall synthesis inhibitors, for example benthiavalicarb,dimethomorph, flumorph, iprovalicarb, mandipropamid, polyoxins,polyoxorim, validamycin A and valifenalate.(10) Lipid and membrane synthesis inhibitors, for example biphenyl,chloroneb, dicloran, edifenphos, etridiazole, iodocarb, iprobenfos,isoprothiolane, propamocarb, propamocarb hydrochloride, prothiocarb,pyrazophos, quintozene, tecnazene and tolclofos-methyl.(11) Melanin biosynthesis inhibitors, for example carpropamid,diclocymet, fenoxanil, phthalide, pyroquilon and tricyclazole.(12) Nucleic acid synthesis inhibitors, for example benalaxyl,benalaxyl-M (kiralaxyl), bupirimate, clozylacon, dimethirimol,ethirimol, furalaxyl, hymexazol, metalaxyl, metalaxyl-M (mefenoxam),ofurace, oxadixyl, oxolinic acid.(13) Signal transduction inhibitors, for example chlozolinate,fenpiclonil, fludioxonil, iprodione, procymidone, quinoxyfen andvinclozolin.(14) Decouplers, for example binapacryl, dinocap, ferimzone, fluazinamand meptyldinocap.(15) Further compounds, for example benthiazole, bethoxazin, capsimycin,carvone, chinomethionat, chlazafenone, cufraneb, cyflufenamid,cymoxanil, cyprosulfamide, dazomet, debacarb, dichlorophen, diclomezine,difenzoquat, difenzoquat methylsulphate, diphenylamine, ecomat,fenpyrazamine, flumetover, fluoromide, flusulfamide, flutianil,fosetyl-aluminium, fosetyl-calcium, fosetyl-sodium, hexachlorobenzene,irumamycin, methasulfocarb, methyl isothiocyanate, metrafenon,mildiomycin, natamycin, nickel dimethyldithiocarbamate,nitrothal-isopropyl, octhilinone, oxamocarb, oxyfenthiin,pentachlorophenol and salts thereof, phenothrin, phosphoric acid andsalts thereof, propamocarb-fosetylate, propanosine-sodium, proquinazid,pyrrolnitrin, tebufloquin, tecloftalam, tolnifanid, triazoxide,trichlamide, zarilamide,1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl 1H-imidazole-1-carboxylate,2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine,2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one,2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone,2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5S)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone,2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(5-phenyl-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone,2-butoxy-6-iodo-3-propyl-4H-chromen-4-one,2-chloro-5-[2-chloro-1-(2,6-difluoro-4-methoxyphenyl)-4-methyl-1H-imidazol-5-yl]pyridine,2-phenylphenol and salts thereof,3,4,5-trichloropyridine-2,6-dicarbonitrile,3-[5-(4-chlorophenyl)-2,3-dimethyl-1,2-oxazolidin-3-yl]pyridine,3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine,4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine,5-amino-1,3,4-thiadiazole-2-thiol,5-chloro-N′-phenyl-N′-(prop-2-yn-1-yl)thiophene-2-sulphonohydrazide,5-methyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidine-7-amine, ethyl(2Z)-3-amino-2-cyano-3-phenylprop-2-enoate,N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloropyridine-3-carboxamide,N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloropyridine-3-carboxamide,N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodopyridine-3-carboxamide,N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1,3-thiazole-4-carboxamide,N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide,N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide,pentyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylidene]amino}oxy)methyl]pyridin-2-yl}carbamate,phenazine-1-carboxylic acid, quinolin-8-ol and quinolin-8-ol sulphate(2:1).(16) Further antimicrobially active compounds: (16.1) benthiazole,(16.2) bethoxazine, (16.3) capsimycin, (16.4) carvone, (16.5)chinomethionat, (16.6) pyriofenone (chlazafenone), (16.7) cufraneb,(16.8) cyflufenamid, (16.9) cymoxanil, (16.10) cyprosulfamide, (16.11)dazomet, (16.12) debacarb, (16.13) dichlorophen, (16.14) diclomezine,(16.15) difenzoquat, (16.16) difenzoquat methylsulphate, (16.17)diphenylamine, (16.18) EcoMate, (16.19) fenpyrazamine, (16.20)flumetover, (16.21) fluoroimide, (16.22) flusulfamide, (16.23)flutianil, (16.24) fosetyl-aluminium, (16.25) fosetyl-calcium, (16.26)fosetyl-sodium, (16.27) hexachlorobenzene, (16.28) irumamycin, (16.29)methasulfocarb, (16.30) methyl isothiocyanate, (16.31) metrafenone,(16.32) mildiomycin, (16.33) natamycin, (16.34) nickeldimethyldithiocarbamate, (16.35) nitrothal-isopropyl, (16.37) oxamocarb,(16.38) oxyfenthiin, (16.39) pentachlorophenol and salts, (16.40)phenothrin, (16.41) phosphoric acid and its salts, (16.42)propamocarb-fosetylate, (16.43) propanosine-sodium, (16.44) pyrimorph,(16.45)(2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one,(16.46)(2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one,(16.47) pyrrolnitrin, (16.48) tebufloquin, (16.49) tecloftalam, (16.50)tolnifanide, (16.51) triazoxide, (16.52) trichlamide, (16.53) zarilamid,(16.54)(3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl2-methylpropanoate, (16.55)1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(16.56)1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(16.57)1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(16.58) 1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl1H-imidazole-1-carboxylate, (16.59)2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine, (16.60)2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one, (16.61)2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetrone,(16.62)2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone,(16.63)2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5S)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone,(16.64)2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(5-phenyl-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone,(16.65) 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, (16.66)2-chloro-5-[2-chloro-1-(2,6-difluoro-4-methoxyphenyl)-4-methyl-1H-imidazol-5-yl]pyridine,(16.67) 2-phenylphenol and salts, (16.68)3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(16.69) 3,4,5-trichloropyridine-2,6-dicarbonitrile, (16.70)3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine,(16.71)4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine,(16.72) 5-amino-1,3,4-thiadiazole-2-thiol, (16.73)5-chloro-N′-phenyl-N′-(prop-2-yn-1-yl)thiophene-2-sulphonohydrazide,(16.74) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidine-4-amine, (16.75)5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidine-4-amine, (16.76)5-methyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidine-7-amine, (16.77) ethyl(2Z)-3-amino-2-cyano-3-phenylacrylate, (16.78)N′-(4-{[3-(4-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(16.79)N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,(16.80)N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,(16.81)N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloronicotinamide,(16.82)N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinamide,(16.83)N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodonicotinamide,(16.84)N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,(16.85)N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,(16.86)N′-{4-[(3-tert-butyl-4-cyano-1,2-thiazol-5-yl)oxy]-2-chloro-5-methylphenyl}-N-ethyl-N-methylimidoformamide,(16.87)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1,3-thiazole-4-carboxamide,(16.88)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide,(16.89)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide,(16.90) pentyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(16.91) phenazine-1-carboxylic acid, (16.92) quinolin-8-ol, (16.93)quinolin-8-ol sulphate (2:1), (16.94) tert-butyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(16.95)1-methyl-3-(trifluoromethyl)-N-[2′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(16.96)N-(4′-chlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(16.97)N-(2′,4′-dichlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(16.98)3-(difluoromethyl)-1-methyl-N-[4′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(16.99)N-(2′,5′-difluorobiphenyl-2-yl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,(16.100)3-(difluoromethyl)-1-methyl-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(16.101)5-fluoro-1,3-dimethyl-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(16.102) 2-chloro-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]nicotinamide,(16.103)3-(difluoromethyl)-N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide,(16.104)N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,(16.105)3-(difluoromethyl)-N-(4′-ethynylbiphenyl-2-yl)-1-methyl-1H-pyrazole-4-carboxamide, (16.106)N-(4′-ethynylbiphenyl-2-yl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,(16.107) 2-chloro-N-(4′-ethynylbiphenyl-2-yl)nicotinamide, (16.108)2-chloro-N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide,(16.109)4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)biphenyl-2-yl]-1,3-thiazole-5-carboxamide,(16.110)5-fluoro-N-[4′-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide,(16.111)2-chloro-N-[4′-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide,(16.112)3-(difluoromethyl)-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide,(16.113)5-fluoro-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide,(16.114)2-chloro-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide,(16.115)(5-bromo-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanone,(16.116)N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N2-(methylsulphonyl)valinamide,(16.117) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (16.118)but-3-yn-1-yl{6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(16.119) 4-amino-5-fluoropyrimidin-2-ol (mesomeric form:4-amino-5-fluoropyrimidin-2(1H)-one), (16.120) propyl3,4,5-trihydroxybenzoate, (16.121)1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(16.122)1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (16.123)1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(16.124)[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(16.125)(S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(16.126)(R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(16.127)2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(16.128)1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (16.129)5-(allylsulphanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(16.130)2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(16.131)2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(16.132)2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(16.133)1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (16.134)1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (16.135)5-(allylsulphanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(16.136)5-(allylsulphanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(16.137)2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(16.138)2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(16.139)2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(16.140)2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(16.141)2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(16.142)2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(16.143)2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(16.144)2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(16.145)2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide,(16.146) 2-(6-benzylpyridin-2-yl)quinazoline, (16.147)2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline,(16.148)3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(16.149) abscisic acid.

The active compounds according to the invention can furthermore becombined with microorganisms. The microorganisms, given good planttolerance, favourable homeotherm toxicity and good environmentalcompatibility, are suitable for protecting plants and plant organs, forincreasing harvest yields, for improving the quality of the harvestedmaterial and for controlling animal pests, especially insects,arachnids, helminths, nematodes and molluscs, which are encountered inagriculture, in horticulture, in animal husbandry, in forests, ingardens and leisure facilities, in the protection of stored products andof materials, and in the hygiene sector. They can preferably be used ascrop protection compositions. They are active against normally sensitiveand resistant species and against all or some stages of development. Theabovementioned microorganisms include:

microorganisms from the group of the bacteria, for example Bacillusagri, Bacillus aizawai, Bacillus albolactis, Bacillus amyloliquefaciens,in particular the strain B. amyloliquefaciens IN937a, or strain FZB42,Bacillus cereus, in particular spores of B. cereus CNCM 1-1562, Bacilluscoagulans, Bacillus endoparasiticus, Bacillus endorhythmos, Bacillusfirmus, in particular spores of B. firmus CNCM I-1582, Bacilluskurstaki, Bacillus lacticola, Bacillus lactimorbus, Bacillus lactis,Bacillus laterosporus, Bacillus lentimorbus, Bacillus licheniformis,Bacillus medusa, Bacillus megaterium, Bacillus metiens, Bacillus natto,Bacillus nigrificans, Bacillus popillae, Bacillus pumilus, in particularthe strain B. pumilus GB34, Bacillus siamensis, Bacillus sphaericus,Bacillus subtilis, in particular the strain B. subtilis GB03, or thestrain B. subtilis var. amyloliquefaciens FZB24, Bacillus thuringiensis,in particular B. thuringiensis var. israelensis or B. thuringiensis ssp.aizawai strain ABTS-1857 or B. thuringiensis ssp kurstaki strain HD-1,B. thuringiensis var. san diego, B. thuringiensis var. tenebrinos,Bacillus uniflagellatus, Delftia acidovorans, in particular strainRAY209, Lysobacter antibioticus, in particular strain 13-1, Metarhiziumanisopliae, Pseudomonas chlororaphis, in particular strain MA342,Pseudomonas proradix, Streptomyces galbus, in particular strain K61,Streptomyces griseoviridis;

microorganisms from the group of the fungi, for example Ampelomycesquisqualis, in particular strain AQ10, Aureobasidium pullulans, inparticular blastospores of strain DSM14940 or blastospores of strainDSM14941 or mixtures thereof, Beauveria bassiana, in particular strainATCC74040, Beauveria brongniartii, Candida oleophila, in particularstrain O, Coniothyrium minitans, in particular strain CON/M/91-8,Dilophosphora alopecuri, Gliocladium catenulatum, in particular strainJ1446; Hirsutella thompsonii, Lagenidium giganteum, Lecanicilliumlecanii (previously known as Verticillium lecanii), in particularconidia of strain KV01, Metarhizium anisopliae, in particular strainF52, Metschnikovia fructicola, in particular strain NRRL Y-30752,Microsphaeropsis ochracea, Muscodor albus, in particular strainQST20799, Nomuraea rileyi, Paecilomyces lilacinus, in particular sporesof strain P. lilacinus 251, Penicillium bilaii, in particular strainATCC22348, Pichia anomala, in particular strain WRL-076, Pseudozymaflocculosa, in particular strain PF-A22 UL, Pytium oligandrum DV74,Trichoderma asperellum, in particular strain ICC012, Trichodermaharzianum, insbesondere T. harzianum T39, Verticillium lecanii, inparticular the strains DAOM198499 and DAOM216596; insecticidalmicroorganisms from the group of the protozoa, for example Nosemalocustae, Vairimorpha;

insecticidal microorganisms from the group of the viruses, for exampleGypsy moth (Lymantria dispar) nuclear polyhedrosis virus (NPV), Tussockmoth (Lymantriidae) NPV, Heliothis NPV, Pine sawfly (Neodiprion) NPV,Codling moth (Cydia pomonella) granulosis virus (GV);microorganisms from the group of the entomopathogenic nematodes, forexample Steinernema scapterisci, Steinernema feltiae (Neoaplectanacarpocapsae), Heterorhabditis heliothidis, Xenorhabdus luminescence.

The active compounds identified here by their common names are known andare described, for example, in the pesticide handbook (“The PesticideManual” 14th Ed., British Crop Protection Council 2006) or can be foundon the Internet (e.g. http://www.alanwood.net/pesticides).

All mixing partners mentioned in classes (1) to (16) can, if they arecapable on the basis of their functional groups, optionally form saltswith suitable bases or acids.

Finally, it has been found that the novel compounds of the formula (I),whilst being well tolerated by plants, with favourable homeothermtoxicity and good environmental compatibility, are suitable inparticular for controlling animal pests, especially arthropods, insects,arachnids, helminths, nematodes and molluscs, which are encountered inagriculture, in forests, in the protection of stored products andmaterials and in the hygiene sector, or in the animal health sector. Thecompounds according to the invention can likewise be used in the animalhealth sector, for example for controlling endo- and/or ectoparasites.

The compounds according to the invention can be used as agents forcontrolling animal pests, preferably as crop protection agents. They areactive against normally sensitive and resistant species and against allor some stages of development.

The compounds according to the invention can be converted into generallyknown formulations. In general, such formulations comprise from 0.01 to98% by weight of active compound, preferably from 0.5 to 90% by weight.

The compounds according to the invention can be present in theircommercially available formulations and in the use forms, prepared fromthese formulations, as a mixture with other active compounds orsynergists. Synergists are compounds which enhance the action of theactive compounds, without any need for the synergist added to be activeitself.

The active compound content of the use forms prepared from thecommercially available formulations may vary within wide limits. Theactive compound concentration of the use forms may be from 0.00000001 to95% by weight of active compound, preferably from 0.00001 to 1% byweight.

The compounds are employed in a customary manner appropriate for the useforms.

All plants and plant parts can be treated in accordance with theinvention. Plants are understood here to mean all plants and plantpopulations, such as desired and undesired wild plants or crop plants(including naturally occurring crop plants). Crop plants can be plantswhich can be obtained by conventional breeding and optimization methodsor by biotechnological and genetic engineering methods or combinationsof these methods, including the transgenic plants and including theplant varieties which can or cannot be protected by varietal propertyrights. Plant parts are to be understood as meaning all above-ground andbelow-ground parts and organs of plants, such as shoot, leaf, flower androot, examples which may be mentioned being leaves, needles, stems,trunks, flowers, fruit-bodies, fruits and seeds and also roots, tubersand rhizomes. The plant parts also include harvested material andvegetative and generative propagation material, for example cuttings,tubers, rhizomes, slips and seed.

The treatment according to the invention of the plants and plant partswith the active compounds is effected directly or by allowing them toact on the surroundings, habitat or storage space thereof by thecustomary treatment methods, for example by dipping, spraying,evaporating, fogging, scattering, painting on, injecting, and, in thecase of propagation material, especially in the case of seeds, also byapplying one or more coats.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding methods, such as crossing or protoplast fusion, andalso parts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineeringmethods, if appropriate in combination with conventional methods(Genetically Modified Organisms), and parts thereof are treated. Theterms “parts” and “parts of plants” or “plant parts” have beenelucidated above.

More preferably, plants of the plant cultivars which are eachcommercially available or in use are treated in accordance with theinvention. Plant cultivars are to be understood as meaning plants havingnew properties (“traits”) and which have been obtained by conventionalbreeding, by mutagenesis or by recombinant DNA techniques. They may becultivars, biotypes and genotypes.

In the animal health sector, i.e. in the field of veterinary medicine,the active compounds according to the present invention act againstanimal parasites, especially ectoparasites or endoparasites. The term“endoparasites” includes especially helminths such as cestodes,nematodes or trematodes, and protozoa such as coccidia. Ectoparasitesare typically and preferably arthropods, especially insects such asflies (biting and licking), parasitic fly larvae, lice, hair lice, birdlice, fleas and the like; or acaricides such as ticks, for example hardticks or soft ticks, or mites such as scab mites, harvest mites, birdmites and the like.

It has also been found that the compounds according to the inventionhave strong insecticidal action against insects which destroy industrialmaterials. Industrial materials in the present context are understood tomean inanimate materials, such as preferably plastics, adhesives, sizes,papers and cards, leather, wood, processed wood products and coatingcompositions.

In addition, the compounds according to the invention can be used asantifouling compositions, alone or in combinations with other activecompounds.

The active compounds are also suitable for controlling animal pests inthe domestic sector, in the hygiene sector and in the protection ofstored products, especially insects, arachnids and mites, which arefound in enclosed spaces, for example homes, factory halls, offices,vehicle cabins and the like. They can be used to control these pestsalone or in combination with other active compounds and auxiliaries indomestic insecticide products. They are effective against sensitive andresistant species, and against all developmental stages.

Plants are to be understood to mean all plant species, plant cultivarsand plant populations such as wanted and unwanted wild plants or cropplants. Crop plants to be treated according to the invention are plantswhich occur naturally or those which are obtained by conventionalbreeding and optimization methods or by biotechnological and geneticengineering methods or by combining the methods mentioned above. Theterm crop plant does, of course, also include transgenic plants.

Plant cultivars are to be understood as meaning plants having newproperties (traits) and which have been obtained by conventionalbreeding, by mutagenesis or by recombinant DNA techniques or acombination thereof. They can be cultivars, varieties, bio- orgenotypes.

Plant parts are understood to mean all parts and organs of plants aboveand below the ground, such as shoot, leaf, flower and root, inparticular leaves, needles, stalks, stems, flowers, fruit-bodies,fruits, seeds, roots, tubers and rhizomes. The term plant parts alsoincludes harvested material and vegetative and generative propagationmaterial, for example cuttings, tubers, rhizomes, slips and seeds orseed.

In one embodiment according to the invention, naturally occurring plantspecies and plant cultivars, or those obtained by conventional breedingand optimization methods (e.g. crossing or protoplast fusion), and alsoparts thereof, are treated.

In a further embodiment according to the invention, transgenic plantsobtained by genetic engineering methods, if appropriate in combinationwith conventional methods, and parts thereof are treated.

The treatment method according to the invention is preferably employedfor genetically modified organisms such as, for example, plants or plantparts.

Genetically modified plants, so-called transgenic plants, are plants inwhich a heterologous gene has been stably integrated into the genome.

The expression “heterologous gene” essentially means a gene which isprovided or assembled outside the plant and when introduced in thenuclear, chloroplastic or mitochondrial genome gives the transformedplant new or improved agronomic or other properties by expressing aprotein or polypeptide of interest or by downregulating or silencing(an)other gene(s) which (is) are present in the plant (using, forexample, antisense technology, cosuppression technology or RNAinterference—RNAi—technology). A heterologous gene that is present inthe genome is also called a transgene. A transgene that is defined byits particular location in the plant genome is called a transformationor transgenic event.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. For example, the following effects which exceedthe effects actually to be expected are possible: reduced applicationrates and/or widened spectrum of activity and/or increased efficacy ofthe active compounds and compositions which can be used in accordancewith the invention, better plant growth, increased tolerance to high orlow temperatures, increased tolerance to drought or to water or soilsalinity, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, bigger fruits, greaterplant height, greener leaf colour, earlier flowering, higher qualityand/or a higher nutritional value of the harvested products, highersugar concentration within the fruits, better storage stability and/orprocessability of the harvested products.

At certain application rates, the active compound combinations accordingto the invention may also have a strengthening effect on plants.Accordingly, they are suitable for mobilizing the defence system of theplant against attack by unwanted phytopathogenic fungi and/ormicroorganisms and/or viruses. This may optionally be one of the reasonsfor the enhanced activity of the combinations according to theinvention, for example against fungi. Plant-strengthening(resistance-inducing) substances are to be understood as meaning, in thepresent context, those substances or combinations of substances whichare capable of stimulating the defence system of plants in such a waythat, when subsequently inoculated with unwanted phytopathogenic fungiand/or microorganisms and/or viruses, the treated plants display asubstantial degree of resistance to these unwanted phytopathogenic fungiand/or microorganisms and/or viruses. In the present case, unwantedphytopathogenic fungi and/or microorganisms and/or viruses areunderstood as meaning phytopathogenic fungi, bacteria and viruses. Thesubstances according to the invention can therefore be used forprotection of plants from attack by the pathogens mentioned within acertain period of time after treatment. The period of time within whichprotection is effected generally extends from 1 to 10 days, preferably 1to 7 days, after the treatment of the plants with the active compounds.

Plants which are furthermore preferably treated according to theinvention are resistant against one or more biotic stress factors, i.e.said plants have a better defence against animal and microbial pests,such as nematodes, insects, mites, phytopathogenic fungi, bacteria,viruses and/or viroids.

In addition to the plants and plant cultivars mentioned above, it isalso possible to treat those according to the invention which areresistant to one or more abiotic stress factors.

Abiotic stress conditions may include, for example, drought, coldtemperature exposure, heat exposure, osmotic stress, waterlogging,increased soil salinity, increased exposure to minerals, exposure toozone, exposure to strong light, limited availability of nitrogennutrients, limited availability of phosphorus nutrients or shadeavoidance.

Plants and plant cultivars which may also be treated according to theinvention are those plants characterized by enhanced yieldcharacteristics Enhanced yield in these plants may be the result of, forexample, improved plant physiology, improved plant growth anddevelopment, such as water use efficiency, water retention efficiency,improved nitrogen use, enhanced carbon assimilation, improvedphotosynthesis, increased germination efficiency and acceleratedmaturation. Yield can also be affected by improved plant architecture(under stress and non-stress conditions), including early flowering,flowering control for hybrid seed production, seedling vigour, plantsize, internode number and distance, root growth, seed size, fruit size,pod size, pod or ear number, seed number per pod or ear, seed mass,enhanced seed filling, reduced seed dispersal, reduced pod dehiscenceand lodging resistance. Further yield traits include seed composition,such as carbohydrate content, protein content, oil content and oilcomposition, nutritional value, reduction in antinutritional compounds,improved processability and better storage stability.

Plants that may be treated according to the invention are hybrid plantsthat already express the characteristics of heterosis or hybrid vigourwhich results in generally higher yield, vigour, health and resistancetowards biotic and abiotic stresses. Such plants are typically made bycrossing an inbred male-sterile parent line (the female parent) withanother inbred male-fertile parent line (the male parent). Hybrid seedis typically harvested from the male-sterile plants and sold to growers.Male-sterile plants can sometimes (e.g. in maize) be produced bydetasseling, (i.e. the mechanical removal of the male reproductiveorgans or male flowers) but, more typically, male sterility is theresult of genetic determinants in the plant genome. In that case, andespecially when seed is the desired product to be harvested from thehybrid plants, it is typically useful to ensure that male fertility inhybrid plants, which contain the genetic determinants responsible formale sterility, is fully restored. This can be accomplished by ensuringthat the male parents have appropriate fertility restorer genes whichare capable of restoring the male fertility in hybrid plants thatcontain the genetic determinants responsible for male sterility. Geneticdeterminants for male sterility may be located in the cytoplasm.Examples of cytoplasmic male sterility (CMS) were for instance describedfor Brassica species. However, genetic determinants for male sterilitycan also be located in the nuclear genome. Male-sterile plants can alsobe obtained by plant biotechnology methods such as genetic engineering.A particularly useful means of obtaining male-sterile plants isdescribed in WO 89/10396, in which, for example, a ribonuclease such asa barnase is selectively expressed in the tapetum cells in the stamens.Fertility can then be restored by expression in the tapetum cells of aribonuclease inhibitor such as barstar.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may be treated according to the inventionare herbicide-tolerant plants, i.e. plants made tolerant to one or moregiven herbicides. Such plants can be obtained either by genetictransformation, or by selection of plants containing a mutationimparting such herbicide tolerance.

Herbicide-tolerant plants are for example glyphosate-tolerant plants,i.e. plants made tolerant to the herbicide glyphosate or salts thereof.Thus, for example, glyphosate-tolerant plants can be obtained bytransforming the plant with a gene encoding the enzyme5-enolpyruvylshikimate-3-phosphate synthase (EPSPS). Examples of suchEPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonellatyphimurium, the CP4 gene of the bacterium Agrobacterium sp., the genesencoding a petunia EPSPS, a tomato EPSPS, or an Eleusine EPSPS. It canalso be a mutated EPSPS. Glyphosate-tolerant plants can also be obtainedby expressing a gene that encodes a glyphosate oxidoreductase enzyme.Glyphosate-tolerant plants can also be obtained by expressing a genethat encodes a glyphosate acetyltransferase enzyme. Glyphosate-tolerantplants can also be obtained by selecting plants containingnaturally-occurring mutations of the above-mentioned genes.

Other herbicide-resistant plants are for example plants that are madetolerant to herbicides inhibiting the enzyme glutamine synthase, such asbialaphos, phosphinothricin or glufosinate. Such plants can be obtainedby expressing an enzyme detoxifying the herbicide or a mutant of theglutamine synthase enzyme that is resistant to inhibition. One suchefficient detoxifying enzyme is, for example, an enzyme encoding aphosphinothricin acetyltransferase (such as the bar or pat protein fromStreptomyces species for example). Plants expressing an exogenousphosphinothricin acetyltransferase have been described.

Further herbicide-tolerant plants are also plants that have been madetolerant to the herbicides inhibiting the enzyme hydroxyphenylpyruvatedioxygenase (HPPD). Hydroxyphenylpyruvate dioxygenases are enzymes thatcatalyse the reaction in which para-hydroxyphenylpyruvate (HPP) isconverted to homogentisate. Plants tolerant to HPPD inhibitors can betransformed with a gene encoding a naturally-occurring resistant HPPDenzyme, or a gene encoding a mutated HPPD enzyme. Tolerance to HPPDinhibitors can also be obtained by transforming plants with genesencoding certain enzymes enabling the formation of homogentisate despitethe inhibition of the native HPPD enzyme by the HPPD inhibitor.Tolerance of plants to HPPD inhibitors can also be improved bytransforming plants with a gene encoding an enzyme prephenatedehydrogenase in addition to a gene encoding an HPPD-tolerant enzyme.

Further herbicide-resistant plants are plants that have been madetolerant to acetolactate synthase (ALS) inhibitors. Known ALS inhibitorsinclude, for example, sulphonylurea, imidazolinone, triazolopyrimidines,pyrimidinyl oxy(thio)benzoates, and/orsulphonylaminocarbonyltriazolinone herbicides. Different mutations inthe ALS enzyme (also known as acetohydroxy acid synthase, AHAS) areknown to confer tolerance to different herbicides and groups ofherbicides. The production of sulphonylurea-tolerant plants andimidazolinone-tolerant plants has been described in the internationalpublication WO 1996/033270. Further sulphonylurea- andimidazolinone-tolerant plants have also been described, for example, inWO 2007/024782.

Other plants tolerant to imidazolinone and/or sulphonylurea can beobtained by induced mutagenesis, selection in cell cultures in thepresence of the herbicide or mutation breeding.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are insect-resistant transgenic plants, i.e. plants maderesistant to attack by certain target insects. Such plants can beobtained by genetic transformation or by selection of plants containinga mutation imparting such insect resistance.

The term “insect-resistant transgenic plant”, as used herein, includesany plant containing at least one transgene comprising a coding sequenceencoding:

-   1) an insecticidal crystal protein from Bacillus thuringiensis or an    insecticidal portion thereof, such as the insecticidal crystal    proteins compiled online at:    http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/, or    insecticidal portions thereof, e.g., proteins of the Cry protein    classes Cry1Ab, Cry1Ac, Cry1F, Cry2Ab, Cry3Ae, or Cry3Bb or    insecticidal portions thereof; or-   2) a crystal protein from Bacillus thuringiensis or a portion    thereof which is insecticidal in the presence of a second other    crystal protein from Bacillus thuringiensis or a portion thereof,    such as the binary toxin made up of the Cry34 and Cry35 crystal    proteins; or-   3) a hybrid insecticidal protein comprising parts of two different    insecticidal crystal proteins from Bacillus thuringiensis, such as a    hybrid of the proteins of 1) above or a hybrid of the proteins of 2)    above, e.g., the Cry1A.105 protein produced by maize event MON98034    (WO 2007/027777); or-   4) a protein of any one of points 1) to 3) above wherein some,    particularly 1 to 10, amino acids have been replaced by another    amino acid to obtain a higher insecticidal activity to a target    insect species, and/or to expand the range of target insect species    affected, and/or because of changes induced into the encoding DNA    during cloning or transformation, such as the Cry3Bb1 protein in    maize events MON863 or MON88017, or the Cry3A protein in maize event    MIR 604;-   5) an insecticidal secreted protein from Bacillus thuringiensis or    Bacillus cereus, or an insecticidal portion thereof, such as the    vegetative insecticidal proteins (VIP) listed at:    http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/vip.html, for    example proteins from the VIP3Aa protein class; or-   6) a secreted protein from Bacillus thuringiensis or Bacillus cereus    which is insecticidal in the presence of a second secreted protein    from Bacillus thuringiensis or B. cereus, such as the binary toxin    made up of the VIP1A and VIP2A proteins;-   7) a hybrid insecticidal protein comprising parts from different    secreted proteins from Bacillus thuringiensis oder Bacillus cereus,    such as a hybrid of the proteins in 1) above or a hybrid of the    proteins in 2) above; or-   8) a protein of any one of points 1) to 3) above wherein some,    particularly 1 to 10, amino acids have been replaced by another    amino acid to obtain a higher insecticidal activity to a target    insect species, and/or to expand the range of target insect species    affected, and/or because of changes induced into the encoding DNA    during cloning or transformation (while still encoding an    insecticidal protein), such as the VIP3Aa protein in cotton event    COT 102.

Of course, an insect-resistant transgenic plant, as used herein, alsoincludes any plant comprising a combination of genes encoding theproteins of any one of the above classes 1 to 8. In one embodiment, aninsect-resistant plant contains more than one transgene encoding aprotein of any one of the above classes 1 to 8, to expand the range oftarget insect species affected, or to delay insect resistancedevelopment to the plants by using different proteins insecticidal tothe same target insect species but having a different mode of action,such as binding to different receptor binding sites in the insect.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are tolerant to abiotic stress factors. Such plants can beobtained by genetic transformation, or by selection of plants containinga mutation imparting such stress resistance. Particularly useful stresstolerant plants include:

-   a. plants which contain a transgene capable of reducing the    expression and/or the activity of the poly(ADP-ribose) polymerase    (PARP) gene in the plant cells or plants;-   b. plants which contain a stress tolerance-enhancing transgene    capable of reducing the expression and/or the activity of the PARG    encoding genes of the plants or plant cells;-   c. plants which contain a stress tolerance-enhancing transgene    coding for a plant-functional enzyme of the nicotinamide adenine    dinucleotide salvage biosynthesis pathway, including nicotinamidase,    nicotinate phosphoribosyltransferase, nicotinic acid mononucleotide    adenyltransferase, nicotinamide adenine dinucleotide synthetase or    nicotinamide phosphoribosyltransferase.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention show altered quantity, quality and/or storage stability of theharvested product and/or altered properties of specific ingredients ofthe harvested product such as, for example:

-   1) transgenic plants which synthesize a modified starch, which in    its physical-chemical characteristics, in particular the amylose    content or the amylose/amylopectin ratio, the degree of branching,    the average chain length, the side chain distribution, the viscosity    behaviour, the gelling strength, the starch grain size and/or the    starch grain morphology, is changed in comparison with the    synthesised starch in wild type plant cells or plants, so that this    modified starch is better suited for special applications;-   2) transgenic plants which synthesize non starch carbohydrate    polymers or which synthesize non starch carbohydrate polymers with    altered properties in comparison to wild type plants without genetic    modification. Examples are plants which produce polyfructose,    especially of the inulin and levan type, plants which produce    alpha-1,4-glucans, plants which produce alpha-1,6-branched    alpha-1,4-glucans, and plants producing alternan;-   3) transgenic plants which produce hyaluronan.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are plants, such as cotton plants, with altered fibrecharacteristics. Such plants can be obtained by genetic transformation,or by selection of plants containing a mutation imparting such alteredfibre characteristics and include:

-   a) plants, such as cotton plants, containing an altered form of    cellulose synthase genes;-   b) plants, such as cotton plants, containing an altered form of rsw2    or rsw3 homologous nucleic acids;-   c) plants, such as cotton plants, with increased expression of    sucrose phosphate synthase;-   d) plants, such as cotton plants, with increased expression of    sucrose synthase;-   e) plants, such as cotton plants, wherein the timing of the    plasmodesmatal gating at the basis of the fibre cell is altered, for    example through downregulation of fibre-selective β-1,3-glucanase;-   f) plants, such as cotton plants, having fibers with altered    reactivity, e.g. through the expression of    N-acetylglucosaminetransferase gene including nodC, and chitin    synthase genes.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are plants, such as oilseed rape or related Brassica plants,with altered oil profile characteristics. Such plants can be obtained bygenetic transformation or by selection of plants containing a mutationimparting such altered oil characteristics and include:

a) plants, such as oilseed rape plants, which produce oil having a higholeic acid content;b) plants, such as oilseed rape plants, which produce oil having a lowlinolenic acid content;c) plants, such as oilseed rape plants, producing oil having a low levelof saturated fatty acids.

Particularly useful transgenic plants which may be treated according tothe invention are plants which comprise one or more genes which encodeone or more toxins and are the transgenic plants available under thefollowing trade names: YIELD GARD® (for example maize, cotton, soyabeans), KnockOut® (for example maize), BiteGard® (for example maize),BT-Xtra® (for example maize), StarLink® (for example maize), Bollgard®(cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (forexample maize), Protecta® and NewLeaf® (potato). Examples ofherbicide-tolerant plants which may be mentioned are maize varieties,cotton varieties and soya bean varieties which are available under thefollowing trade names: Roundup Ready® (tolerance to glyphosate, forexample maize, cotton, soya beans), Liberty Link® (tolerance tophosphinothricin, for example oilseed rape), IMI® (tolerance toimidazolinone) and SCS® (tolerance to sulphonylurea, for example maize).Herbicide-resistant plants (plants bred in a conventional manner forherbicide tolerance) which may be mentioned include the varieties soldunder the name Clearfield® (for example maize).

Particularly useful transgenic plants which may be treated according tothe invention are plants containing transformation events, or acombination of transformation events, and that are listed for example inthe databases for various national or regional regulatory agencies (seefor example http://gmoinfo.jrc.it/gmp_browse.aspx andhttp://www.agbios.com/dbase.php).

Treatment according to the invention of the plants and plant parts withthe active compound combinations is carried out directly or by allowingthe compounds to act on their surroundings, environment or storage spaceby the customary treatment methods, for example by immersion, spraying,evaporation, fogging, scattering, painting on and, in the case ofpropagation material, in particular in the case of seeds, also byapplying one or more coats.

The mixtures according to the invention are particularly suitable forthe treatment of seed. Here, mention may preferably be made of thecombinations according to the invention mentioned above as preferred orparticularly preferred. Thus, most of the damage to crop plants which iscaused by pests occurs as early as when the seed is infested duringstorage and after the seed is introduced into the soil, and during andimmediately after germination of the plants. This phase is particularlycritical since the roots and shoots of the growing plant areparticularly sensitive and even minor damage can lead to the death ofthe whole plant. Protecting the seed and the germinating plant by theuse of suitable compositions is therefore of particularly greatinterest.

The control of pests by treating the seed of plants has been known for along time and is the subject of continuous improvements. However, thetreatment of seed entails a series of problems which cannot always besolved in a satisfactory manner. Thus, it is desirable to developmethods for protecting the seed and the germinating plant which dispensewith the additional application of crop protection compositions aftersowing or after emergence of the plants. It is furthermore desirable tooptimize the amount of active compound employed in such a way as toprovide optimum protection for the seed and the germinating plant fromattack by pests, but without damaging the plant itself by the activecompound employed. In particular, methods for the treatment of seedshould also take into consideration the intrinsic insecticidalproperties of transgenic plants in order to achieve optimum protectionof the seed and also the germinating plant with a minimum of cropprotection compositions being employed.

The present invention therefore in particular also relates to a methodfor the protection of seed and germinating plants from attack by pests,by treating the seed with a composition according to the invention. Theinvention likewise relates to the use of the compositions according tothe invention for the treatment of seed for protecting the seed and theresulting plant from pests. The invention further relates to seed whichhas been treated with a composition according to the invention forprotection from pests.

One of the advantages of the present invention is that the particularsystemic properties of the compositions according to the invention meanthat treatment of the seed with these compositions not only protects theseed itself, but also the resulting plants after emergence, from pests.In this way, the immediate treatment of the crop at the time of sowingor shortly thereafter can be dispensed with.

A further advantage is the synergistically increased insecticidalactivity of the compositions according to the invention in comparisonwith the individual insecticidally active compound, which exceeds theexpected activity of the two active compounds when applied individually.Also advantageous is the synergistic enhancement of the fungicidalactivity of the compositions according to the invention compared withthe individual fungicidally active compound, which exceeds the expectedactivity of the active compound applied individually. This makespossible an optimization of the amount of active compounds employed.

Furthermore, it must be considered as advantageous that the mixturesaccording to the invention can also be employed in particular intransgenic seed, the plants arising from this seed being capable ofexpressing a protein directed against pests. By treating such seed withthe compositions according to the invention, certain pests can becontrolled merely by the expression of the, for example, insecticidalprotein, and additionally damage to the seed may be averted by thecompositions according to the invention.

The compositions according to the invention are suitable for protectingseed of any plant variety as already mentioned above which is employedin agriculture, in the greenhouse, in forests or in horticulture. Inparticular, this takes the form of seed of maize, peanut, canola,oilseed rape, poppy, soya, cotton, beet (for example sugar beet andfodder beet), rice, millet, wheat, barley, oats, rye, sunflower,tobacco, potatoes or vegetables (for example tomatoes, cabbage species).The compositions according to the invention are likewise suitable fortreating the seed of fruit plants and vegetables as already mentionedabove. The treatment of the seed of maize, soya, cotton, wheat andcanola or oilseed rape is of particular importance.

As already mentioned above, the treatment of transgenic seed with acomposition according to the invention is also of particularsignificance. This takes the form of seed of plants which, as a rule,comprise at least one heterologous gene which governs the expression ofa polypeptide with in particular insecticidal properties. In thiscontext, the heterologous genes in transgenic seed may be derived frommicroorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia,Trichoderma, Clavibacter, Glomus or Gliocladium. The present inventionis particularly suitable for the treatment of transgenic seed whichcomprises at least one heterologous gene originating from Bacillus sp.and whose gene product shows activity against the European corn borerand/or the corn root worm. The gene involved is more preferably aheterologous gene which originates from Bacillus thuringiensis.

Within the context of the present invention, the composition accordingto the invention is applied to the seed either alone or in a suitableformulation. Preferably, the seed is treated in a state in which it isstable enough to avoid damage during treatment. In general, the seed canbe treated at any time between harvest and sowing. The seed usually usedhas been separated from the plant and freed from cobs, shells, stalks,coats, hairs or the flesh of the fruits.

When treating the seed, it generally has to be ensured that the amountof the composition according to the invention applied to the seed and/orthe amount of further additives is selected such that the germination ofthe seed is not impaired, or that the resulting plant is not damaged.This must be ensured particularly in the case of active compounds whichcan exhibit phytotoxic effects at certain application rates.

In addition, the compounds according to the invention can be used tocontrol a multitude of different pests, including, for example, harmfulsucking insects, biting insects and other pests which are plantparasites, stored material pests, pests which destroy industrialmaterials, and hygiene pests including parasites in the animal healthsector, and for the control thereof, for example the elimination anderadication thereof. The present invention thus also includes a methodfor controlling pests.

In the animal health sector, i.e. in the field of veterinary medicine,the active compounds according to the present invention act againstanimal parasites, especially ectoparasites or endoparasites. The term“endoparasites” includes especially helminths such as cestodes,nematodes or trematodes, and protozoa such as coccidia. Ectoparasitesare typically and preferably arthropods, especially insects such asflies (biting and licking), parasitic fly larvae, lice, hair lice, birdlice, fleas and the like; or acaricides such as ticks, for example hardticks or soft ticks, or mites such as scab mites, harvest mites, birdmites and the like.

These parasites include:

From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phthirus spp., Solenopotes spp.;specific examples are: Linognathus setosus, Linognathus vituli,Linognathus ovillus, Linognathus oviformis, Linognathus pedalis,Linognathus stenopsis, Haematopinus asini macrocephalus, Haematopinuseurysternus, Haematopinus suis, Pediculus humanus capitis, Pediculushumanus corporis, Phylloera vastatrix, Phthirus pubis, Solenopotescapillatus;

From the order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp., Felicola spp.; specific examples are: Bovicola bovis,Bovicola ovis, Bovicola limbata, Damalina bovis, Trichodectes canis,Felicola subrostratus, Bovicola caprae, Lepikentron ovis, Werneckiellaequi;

From the order of the Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Odagmia spp., Wilhelmia spp., Hybomitraspp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp.,Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp.,Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Luciliaspp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp.,Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp.,Melophagus spp., Rhinoestrus spp., Tipula spp.; specific examples are:Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anophelesgambiae, Anopheles maculipennis, Calliphora erythrocephala, Chrysozonapluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Fanniacanicularis, Sarcophaga carnaria, Stomoxys calcitrans, Tipula paludosa,Lucilia cuprina, Lucilia sericata, Simulium reptans, Phlebotomuspapatasi, Phlebotomus longipalpis, Odagmia ornata, Wilhelmia equina,Boophthora erythrocephala, Tabanus bromius, Tabanus spodopterus, Tabanusatratus, Tabanus sudeticus, Hybomitra ciurea, Chrysops caecutiens,Chrysops relictus, Haematopota pluvialis, Haematopota italica, Muscaautumnalis, Musca domestica, Haematobia irritans irritans, Haematobiairritans exigua, Haematobia stimulans, Hydrotaea irritans, Hydrotaeaalbipuncta, Chrysomya chloropyga, Chrysomya bezziana, Oestrus ovis,Hypoderma bovis, Hypoderma lineatum, Przhevalskiana silenus, Dermatobiahominis, Melophagus ovinus, Lipoptena capreoli, Lipoptena cervi,Hippobosca variegata, Hippobosca equina, Gasterophilus intestinalis,Gasterophilus haemorroidalis, Gasterophilus inermis, Gasterophilusnasalis, Gasterophilus nigricornis, Gasterophilus pecorum, Braula coeca;From the order of the Siphonapterida, for example, Pulex spp.,Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp.;specific examples are: Ctenocephalides canis, Ctenocephalides felis,Pulex irritans, Tunga penetrans, Xenopsylla cheopis;From the order of the Heteropterida, for example, Cimex spp., Triatomaspp., Rhodnius spp., Panstrongylus spp.From the order of the Blattarida, for example, Blatta orientalis,Periplaneta americana, Blattela germanica and Supella spp. (e.g.Suppella longipalpa);From the subclass of the Acari (Acarina) and the orders of the Meta- andMesostigmata, for example, Argas spp., Ornithodorus spp., Otobius spp.,Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp., Dermacentorspp., Haemophysalis spp., Hyalomma spp., Dermanyssus spp., Rhipicephalusspp. (the original genus of multihost ticks), Ornithonyssus spp.,Pneumonyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp.,Varroa spp., Acarapis spp.; specific examples are: Argas persicus, Argasreflexus, Ornithodorus moubata, Otobius megnini, Rhipicephalus(Boophilus) microplus, Rhipicephalus (Boophilus) decoloratus,Rhipicephalus (Boophilus) annulatus, Rhipicephalus (Boophilus)calceratus, Hyalomma anatolicum, Hyalomma aegypticum, Hyalommamarginatum, Hyalomma transiens, Rhipicephalus evertsi, Ixodes ricinus,Ixodes hexagonus, Ixodes canisuga, Ixodes pilosus, Ixodes rubicundus,Ixodes scapularis, Ixodes holocyclus, Haemaphysalis concinna,Haemaphysalis punctata, Haemaphysalis cinnabarina, Haemaphysalisotophila, Haemaphysalis leachi, Haemaphysalis longicorni, Dermacentormarginatus, Dermacentor reticulatus, Dermacentor pictus, Dermacentoralbipictus, Dermacentor andersoni, Dermacentor variabilis, Hyalommamauritanicum, Rhipicephalus sanguineus, Rhipicephalus bursa,Rhipicephalus appendiculatus, Rhipicephalus capensis, Rhipicephalusturanicus, Rhipicephalus zambeziensis, Amblyomma americanum, Amblyommavariegatum, Amblyomma maculatum, Amblyomma hebraeum, Amblyommacajennense, Dermanyssus gallinae, Ornithonyssus bursa, Ornithonyssussylviarum, Varroa jacobsoni;From the order of the Actinedida (Prostigmata) and Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.; specificexamples are: Cheyletiella yasguri, Cheyletiella blakei, Demodex canis,Demodex bovis, Demodex ovis, Demodex caprae, Demodex equi, Demodexcaballi, Demodex suis, Neotrombicula autumnalis, Neotrombicula desaleri,Neoschongastia xerothermobia, Trombicula akamushi, Otodectes cynotis,Notoedres cati, Sarcoptis canis, Sarcoptes bovis, Sarcoptes ovis,Sarcoptes rupicaprae (=S. caprae), Sarcoptes equi, Sarcoptes suis,Psoroptes ovis, Psoroptes cuniculi, Psoroptes equi, Chorioptes bovis,Psoergates ovis, Pneumonyssoidic mange, Pneumonyssoides caninum,Acarapis woodi.

The active compounds according to the invention are also suitable forcontrolling arthropods, helminths and protozoa which attack animals. Theanimals include agricultural livestock, for example cattle, sheep,goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens,turkeys, ducks, geese, cultured fish, honey bees. The animals alsoinclude domestic animals—also referred to as companion animals—forexample dogs, cats, caged birds, aquarium fish, and what are known astest animals, for example hamsters, guinea pigs, rats and mice.

The control of these arthropods, helminths and/or protozoa should reducecases of death and improve the performance (for meat, milk, wool, hides,eggs, honey etc.) and the health of the host animal, and so the use ofthe active compounds according to the invention enables moreeconomically viable and easier animal husbandry.

For example, it is desirable to prevent or to interrupt the uptake ofblood from the host by the parasites (if relevant). Control of theparasites can also contribute to preventing the transmission ofinfectious substances.

The term “control” as used herein with regard to the field of animalhealth means that the active compounds act by reducing the occurrence ofthe parasite in question in an animal infested with such parasites to aharmless level. More specifically, “control” as used herein means thatthe active compound kills the parasite in question, retards its growthor inhibits its proliferation.

In general, the active compounds according to the invention can beemployed directly when they are used for the treatment of animals. Theyare preferably employed in the form of pharmaceutical compositions whichmay comprise pharmaceutically acceptable excipients and/or auxiliariesknown in the prior art.

In the sector of animal health and in animal husbandry, the activecompounds are employed (administered) in a known manner, by enteraladministration in the form of, for example, tablets, capsules, potions,drenches, granules, pastes, boluses, the feed-through process andsuppositories, by parenteral administration, for example by injection(intramuscular, subcutaneous, intravenous, intraperitoneal inter alia),implants, by nasal administration, by dermal administration in the form,for example, of dipping or bathing, spraying, pouring on and spottingon, washing and powdering, and also with the aid of moulded articlescontaining the active compound, such as collars, earmarks, tailmarks,limb bands, halters, marking devices, etc. The active compounds can beformulated as a shampoo or as suitable formulations applicable inaerosols or unpressurized sprays, for example pump sprays and atomizersprays.

In the case of employment for livestock, poultry, domestic pets, etc.,the active compounds according to the invention can be employed asformulations (for example powders, wettable powders [“WP”], emulsions,emulsifiable concentrates [“EC”], free-flowing compositions, homogeneoussolutions and suspension concentrates [“SC”]), which contain the activecompounds in an amount of 1 to 80% by weight, directly or after dilution(e.g. 100- to 10 000-fold dilution), or they can be used as a chemicalbath.

In the case of use in the animal health sector, the active compoundsaccording to the invention can be used in combination with suitablesynergists or other active compounds, for example acaricides,insecticides, anthelmintics, anti-protozoal agents.

The compounds according to the invention can be prepared by customarymethods known to those skilled in the art.

Reaction Scheme 1 shows the general Preparation Process A for thecompounds (I-1) according to the invention.

The radicals A₁-A₄, R¹, M¹, M², Q and Z¹-Z³ have the meanings describedabove. PG represents a suitable protective group, e.g. t-butoxycarbonyl.LG represents a leaving group, e.g. chlorine. The five-membered cyclesof E1-E3, carbon and nitrogen represent the 5-membered heterocyclesdefined under T. X represents a halogen, e.g. fluorine. U representsbromine, iodine or triflate if M represents a boronic acid, boronicester or trifluoroboronate. U represents a boronic acid, boronic esteror trifluoroboronate if M represents bromine, iodine or triflate.

Compounds according to the invention of the general structure (I-1) canbe prepared by processes known from the literature by reactingintermediate 7 with acylating agents of the general structure 8[WO2010-051926; WO2010-133312]. Intermediates of the general structure 7can be prepared from N-protected derivatives of the general structure 6.Compounds of the general structure 6 can be prepared bypalladium-catalysed reactions from the reaction partners 4 and 5[WO2005-040110; WO2009-089508]. The compounds of the general structure 5are either commercially available or can be prepared by processes knownto the person skilled in the art. The compounds of the general structure4 can be prepared by processes known from the literature either bynucleophilic substitution at the aromatic ring (X=chlorine or fluorine)[WO2007-107470; Tetrahedron Letters 2003, 44, 7629-7632] or by atransition metal-catalysed reaction (X=bromine or iodine)[WO2012-003405; WO2009-158371] from the appropriate starting materials 2and 3.

Alternatively, the compounds (I-1-1) according to the invention can beprepared by the general Preparation Process B (Reaction Scheme 2).

The radicals A₁-A₄, R¹, Q and Z¹-Z³ have the meanings described above.PG represents a suitable protective group, e.g. t-butoxycarbonyl. LGrepresents a leaving group, e.g. chlorine. The five-membered cycles ofE1-E3, carbon and nitrogen represent the 5-membered heterocycles definedunder T. X represents a halogen, e.g. fluorine. U represents bromine,iodine or triflate if M represents a boronic acid, boronic ester ortrifluoroboronate. U represents a boronic acid, boronic ester ortrifluoroboronate if M represents bromine, iodine or triflate.

Compounds according to the invention of the general structure (I-1-1)can be prepared analogously to peptide coupling methods known from theliterature from starting materials 8 and 7a [WO2010-051926;WO2010-133312]. Alternatively, the compounds according to the inventionof the general structure (I-1-1) can also be prepared directly fromcompounds of the general structure 10 by processes known from theliterature [Tetrahedron Letters 2000, 41(18), 3513-3516; Journal of theAmerican Chemical Society 1925, 47, 3051-7]. Depending on the protectivegroup used, compounds of the general structure 7a can be prepared bysuitable deprotection of the amino function from compounds of thegeneral structure 6a [Green's Protective Groups in Organic Synthesis,4th Edition, P. G. M. Wuts, T. W. Greene, John Wiley & Sons, Inc.,Hoboken, N.J., USA]. Compounds of the general structure 6a can beprepared analogously to processes known from the literature fromcompounds of the general structure 10 [Tetrahedron 2003, 59(29),5417-5423; Journal of Medicinal Chemistry 2013, 56(5), 1946-1960].Compounds of the general structure 10 can be prepared analogously to theabove-described synthesis of 6. The preparation of the compounds of thegeneral structure 4 has already been discussed in the PreparationProcess.

Compounds according to the invention of the general structure (I-2) canbe synthesized by the Preparation Process C shown in Reaction Scheme 3.

The radicals A₁-A₄, Q, R¹ and Z¹-Z³ have the meanings described above.The five-membered cycles of E1-E3, carbon and nitrogen represent the5-membered heterocycles defined under T.

Compounds according to the invention of the general structure (I-2) canbe prepared analogously to processes known from the literature fromcompounds of the general structure (I-1) [WO2012-056372; WO2003-066050].

Compounds according to the invention of the general structure (II) canbe synthesized by the Preparation Process D shown in Reaction Scheme 4.

The radicals A₁-A₄, R¹, Q and Z¹-Z³ have the meanings described above.LG represents a leaving group, e.g. chlorine. The five-membered cyclesof E1-E3, carbon and nitrogen represent the 5-membered heterocyclesdefined under T.

Compounds according to the invention of the general structure II can beprepared analogously to processes known from the literature fromcompounds of the general structure 7a and 11 [US2007/0117858;WO2013/068462; US2009/0233878]

The compounds of the general structure 5 are either commerciallyavailable or can be prepared by processes known to the person skilled inthe art or analogously to these processes [WO2012004217; WO2009-130475;WO2008-107125; WO2003-099805; WO2012-0225061; WO2009-010488].

The compounds of the general structure 2 are either commerciallyavailable or can be prepared by processes known to the person skilled inthe art or analogously to these processes [WO2010-051926; WO2011-131615;WO2006-018725; WO2012-065932; WO2007077961; US2012-0115903;WO2010-017902; WO2010-127856; Tetrahedron Letters 2011, 44, 8451-8457].

The compounds of the general structure 3 are either commerciallyavailable or can be prepared by processes known to the person skilled inthe art or analogously to these processes.

Oxidizing agents for the oxidation of alcoholic groups are known (cf.,for example, oxidizing agents in Organic Synthesis by Oxidation withMetal Compounds, Mijs, de Jonge, Plenum Verlag, New York, 1986;Manganese Compounds as Oxidizing Agents in Organic Chemistry, Arndt,Open Court Publishing Company, La Salle, Ill., 1981; The Oxidation ofOrganic Compounds by Permanganate Ion and Hexavalent Chromium, Lee, OpenCourt Publishing Company, La Salle, Ill., 1980). An oxidation can becarried out, for example, in the presence of permanganates (for examplepotassium permanganate), metal oxides (for example manganese dioxide,chromium oxides which are used, for example, in dipyridinechromium(VI)oxide as Collins reagent (cf. J. C. Collins et al., Tetrahedron Lett.30, 3363-3366, 1968)). Likewise in the presence of pyridiniumchlorochromate (for example Corey's reagent) (cf. also R. O. Hutchins etal., Tetrahedron Lett. 48, 4167-4170, 1977; D. Landini et al. Synthesis134-136, 1979) or ruthenium tetroxide (cf. S.-I. Murahashi, N. KomiyaRuthenium-catalyzed Oxidation of Alkenes, Alcohols, Amines, Amides,β-Lactams, Phenols and Hydrocarbons, in: Modern Oxidation Methods,Baeckvall, Jan-Erling (Eds.), Wiley-VCH-Verlag GmbH & Co. KGaA, 2004).Likewise suitable are ultrasound-induced oxidation reactions and the useof potassium permanganate (cf. J. Yamawaki et al., Chem. Lett. 3,379-380, 1983).

All known suitable acidic or basic reaction auxiliaries can be usedaccording to the procedures described in the literature todeblock/remove the protective group SG. When protective groups of thecarbamate type are used for amino groups, preference is given to usingacidic reaction auxiliaries. When the t-butylcarbamate protective group(BOC group) is employed, for example, mixtures of mineral acids such ashydrochloric acid, hydrobromic acid, nitric acid, sulphuric acid,phosphoric acid or organic acids such as benzoic acid, formic acid,acetic acid, trifluoroacetic acid, methanesulphonic acid,benzenesulphonic acid or toluenesulphonic acid and a suitable diluentsuch as water and/or an organic solvent such as tetrahydrofuran,dioxane, dichloromethane, chloroform, ethyl acetate, ethanol or methanolare used. Preference is given to mixtures of hydrochloric acid or aceticacid with water and/or an organic solvent such as ethyl acetate.

It is known that certain reactions and preparation processes can becarried out particularly efficiently in the presence of diluents orsolvents and basic or acidic reaction auxiliaries. It is also possibleto use mixtures of the diluents or solvents. The diluents or solventsare advantageously employed in such an amount that the reaction mixtureis readily stirrable during the entire process.

Suitable diluents or solvents for carrying out the processes accordingto the invention are, in principle, all organic solvents which are inertunder the specific reaction conditions. Examples include:halohydrocarbons (for example chlorohydrocarbons such astetrachloroethylene, tetrachloroethane, dichloropropane, methylenechloride, dichlorobutane, chloroform, carbon tetrachloride,trichloroethane, trichloroethylene, pentachloroethane, difluorobenzene,1,2-dichloro ethane, chlorobenzene, bromobenzene, dichlorobenzene,chlorotoluene, trichlorobenzene), alcohols (for example methanol,ethanol, isopropanol, butanol), ethers (for example ethyl propyl ether,methyl tert-butyl ether, n-butyl ether, anisole, phenetole, cyclohexylmethyl ether, dimethyl ether, diethyl ether, dipropyl ether, diisopropylether, di-n-butyl ether, diisobutyl ether, diisoamyl ether, ethyleneglycol dimethyl ether, tetrahydrofuran, dioxane, dichlorodiethyl etherand polyethers of ethylene oxide and/or propylene oxide), amines (forexample trimethyl-, triethyl-, tripropyl-, tributylamine,N-methylmorpholine, pyridine and tetramethylenediamine),nitrohydrocarbons (for example nitromethane, nitroethane, nitropropane,nitrobenzene, chloronitrobenzene, o-nitrotoluene); nitriles (for exampleacetonitrile, propionitrile, butyronitrile, isobutyronitrile,benzonitrile, m-chlorobenzonitrile), tetrahydrothiophene dioxide,dimethyl sulphoxide, tetramethylene sulphoxide, dipropyl sulphoxide,benzyl methyl sulphoxide, diisobutyl sulphoxide, dibutyl sulphoxide,diisoamyl sulphoxide, sulphones (for example dimethyl, diethyl,dipropyl, dibutyl, diphenyl, dihexyl, methyl ethyl, ethyl propyl, ethylisobutyl and pentamethylene sulphone), aliphatic, cycloaliphatic oraromatic hydrocarbons (for example pentane, hexane, heptane, octane,nonane and technical hydrocarbons), and also what are called “whitespirits” with components having boiling points in the range from, forexample, 40° C. to 250° C., cymene, petroleum fractions within a boilingrange from 70° C. to 190° C., cyclohexane, methylcyclohexane, petroleumether, ligroin, octane, benzene, toluene, chlorobenzene, bromobenzene,nitrobenzene, xylene, esters (for example methyl, ethyl, butyl andisobutyl acetate, dimethyl, dibutyl and ethylene carbonate); amides (forexample hexamethylphosphoric triamide, formamide, N-methylformamide,N,N-dimethylformamide, N,N-dipropylformamide, N,N-dibutylformamide,N-methylpyrrolidine, N-methylcaprolactam,1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidine, octylpyrrolidone,octylcaprolactam, 1,3-dimethyl-2-imidazolinedione, N-formylpiperidine,N,N′-diformylpiperazine) and ketones (for example acetone, acetophenone,methyl ethyl ketone, methyl butyl ketone).

The basic reaction auxiliaries used to perform the processes accordingto the invention may be all suitable acid binders. Examples include:alkaline earth metal or alkali metal compounds (e.g. hydroxides,hydrides, oxides and carbonates of lithium, sodium, potassium,magnesium, calcium and barium), amidine bases or guanidine bases (e.g.7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD);diazabicyclo[4.3.0]nonene (DBN), diazabicyclo[2.2.2]octane (DABCO),1,8-diazabicyclo[5.4.0]undecene (DBU), cyclohexyltetrabutylguanidine(CyTBG), cyclohexyltetramethylguanidine (CyTMG),N,N,N,N-tetramethyl-1,8-naphthalenediamine, pentamethylpiperidine) andamines, especially tertiary amines (e.g. triethylamine, trimethylamine,tribenzylamine, triisopropylamine, tributylamine, tricyclohexylamine,triamylamine, trihexylamine, N,N-dimethylaniline, N,N-dimethyltoluidine,N,N-dimethyl-p-aminopyridine, N-methylpyrrolidine, N-methylpiperidine,N-methylimidazole, N-methylpyrazole, N-methylmorpholine,N-methylhexamethylenediamine, pyridine, 4-pyrrolidinopyridine,4-dimethylaminopyridine, quinoline, α-picoline, β-picoline,isoquinoline, pyrimidine, acridine, N,N,N′,N′-tetramethylenediamine,N,N,N′,N′-tetraethylenediamine, quinoxaline, N-propyldiisopropylamine,N-ethyldiisopropylamine, N,N′-dimethylcyclohexylamine, 2,6-lutidine,2,4-lutidine or triethyldiamine).

The acidic reaction auxiliaries used to perform the processes accordingto the invention include all mineral acids (e.g. hydrohalic acids suchas hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydriodicacid, and also sulphuric acid, phosphoric acid, phosphorous acid, nitricacid), Lewis acids (e.g. aluminium(III) chloride, boron trifluoride orits etherate, titanium(IV) chloride, tin(IV) chloride) and organic acids(e.g. formic acid, acetic acid, propionic acid, malonic acid, lacticacid, oxalic acid, fumaric acid, adipic acid, stearic acid, tartaricacid, oleic acid, methanesulphonic acid, benzoic acid, benzenesulphonicacid or para-toluenesulphonic acid).

If protective groups are intended in the reaction schemes, all generallyknown protective groups may be used. In particular those described byGreene T. W., Wuts P. G. W. in Protective Groups in Organic Synthesis;John Wiley & Sons, Inc. 1999, “Protection for the hydroxyl groupincluding 1,2- and 1,3-diols”.

Also suitable are protective groups

of the substituted methyl ether type (for example methoxymethyl ether(MOM), methylthiomethyl ether (MTM), (phenyldimethylsilyl)methoxymethylether (SNOM-OR), benzyloxymethyl ether (BOM-OR)para-methoxybenzyloxymethyl ether (PMBM-OR), para-nitrobenzyloxymethylether, ortho-nitrobenzyloxymethyl ether (NBOM-OR),(4-methoxyphenoxy)methyl ether (p-AOM-OR), guaiacolmethyl ether(GUM-OR), t-butoxymethyl ether, 4-pentyloxymethyl ether (POM-OR),silyloxymethyl ether, 2-methoxyethoxymethyl ether (MEM-OR),2,2,2-trichloroethoxymethyl ether, bis(2-chloroethoxy)methyl ether,2-(trimethylsilyl)ethoxymethyl ether (SEM-OR), methoxymethyl ether(MM-OR));of the substituted ethyl ether type (for example 1-ethoxyethyl ether(EE-OR), 1-(2-chloroethoxy)ethyl ether (CEE-OR),1-[2-(trimethylsilyl)ethoxy]ethyl ether (SEE-OR),1-methyl-1-methoxyethyl ether (MIP-OR), 1-methyl-1-benzyloxyethyl ether(MBE-OR), 1-methyl-1-benzyloxy-2-fluorpethyl ether (MIP-OR),1-methyl-1-phenoxyethyl ether, 2,2,2-trichloroethyl ether,1,1-dianisyl-2,2,2-trichloroethyl ether (DATE-OR),1,1,1,3,3,3-hexafluoro-2-phenylisopropyl ether (HIP-OR),2-trimethylsilylethyl ether, 2-(benzylthio)ethyl ether,2-(phenylselenyl)ethyl ether), an ether (for example tetrahydropyranylether (THP-OR), 3-bromotetrahydropyranyl ether (3-BrTHP-OR),tetrahydrothiopyranyl ether, 1-methoxycyclohexyl ether, 2- and 4-picolylether, 3-methyl-2-picolyl-N-oxido ether, 2-quinolinylmethyl ether(Qm-OR), 1-pyrenylmethyl ether, diphenylmethyl ether (DPM-OR), para,para′-dinitrobenzhydryl ether (DNB-OR), 5-dibenzosuberyl ether,triphenylmethyl ether (Tr-OR), alpha-naphthyldiphenylmethyl ether,para-methoxyphenyldiphenylmethyl ether (MMTrOR),di(para-methoxyphenyl)phenylmethyl ether (DMTr-OR),tri(para-methoxyphenyl)phenylmethyl ether (TMTr-OR),4-(4′-bromophenacyloxy)phenyldiphenylmethyl ether,4,4′,4″-tris(4,5-dichlorophthalimidophenyl)methyl ether (CPTr-OR),4,4′,4″-tris(benzoyloxyphenyl)methyl ether (TBTr-OR),4,4′-dimethoxy-3″-[N-(imidazolylmethyl)]trityl ether (IDTr-OR),4,4′-dimethoxy-3″-[N-(imidazolylethyl)carbamoyl]trityl ether (IETr-OR),1,1-bis(4-methoxyphenyl)-1′-pyrenylmethyl ether (Bmpm-OR), 9-anthrylether, 9-(9-phenyl)xanthenyl ether (Pixyl-OR),9-(9-phenyl-10-oxo)anthryl (tritylone ether), 4-methoxytetrahydropyranylether (MTHP-OR), 4-methoxytetrahydrothiopyranyl ether,4-methoxytetrahydrothiopyranyl S,S-dioxide,1-[(2-chloro-4-methyl)phenyl]-4-methoxypiperidin-4-yl ether (CTMP-OR),1-(2-fluorophenyl)-4-methoxypiperidin-4-yl ether (Fpmp-OR),1,4-dioxan-2-yl ether, tetrahydrofuranyl ether, tetrahydrothiofuranylether,2,3,3a,4,5,6,7,7a-octahydro-7,8,8-trimethyl-4,7-methanebenzofuran-2-ylether (MBF-OR), t-butyl ether, allyl ether, propargyl ether,para-chlorophenyl ether, para-methoxyphenyl ether, para-nitrophenylether, para-2,4-dinitrophenyl ether (DNP-OR),2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl ether, benzyl ether(Bn-OR));of the substituted benzyl ether type (for example para-methoxybenzylether (MPM-OR), 3,4-dimethoxybenzyl ether (DMPM-OR), ortho-nitrobenzylether, para-nitrobenzyl ether, para-halobenzyl ether, 2,6-dichlorobenzylether, para-aminoacylbenzyl ether (PAB-OR), para-azidobenzyl ether(Azb-OR), 4-azido-3-chlorobenzyl ether, 2-trifluoromethylbenzyl ether,para-(methylsulphinyl)benzyl ether (Msib-OR));of the silyl ether type (for example trimethylsilyl ether (TMS-OR),triethylsilyl ether (TES-OR), triisopropylsilyl ether (TIPS-OR),dimethylisopropylsilyl ether (IPDMS-OR), diethylisopropylsilyl ether(DEIPS-OR), dimethylhexylsilyl ether (TDS-OR), t-butyldimethylsilylether (TBDMS-OR), t-butyldiphenylsilyl ether (TBDPS-OR), tribenzylsilylether, tri-para-xylylsilyl ether, triphenylsilyl ether (TPS-OR),diphenylmethylsilyl ether (DPMS-OR), di-t-butylmethylsilyl ether(DTBMS-OR), tris(trimethylsilyl)silyl ether (sisyl ether),di-t-butylmethylsilyl ether (DTBMS-OR), tris(trimethylsilyl)silyl ether(sisyl ether), (2-hydroxystyryl)dimethylsilyl ether (HSDMS-OR),(2-hydroxystyryl)diisopropylsilyl ether (HSDIS-OR),t-butylmethoxyphenylsilyl ether (TBMPS-OR), t-butoxydiphenylsilyl ether(DPTBOS-OR));of the ester type (for example formate ester, benzoylformate ester,acetate ester (Ac-OR), chloroacetate ester, dichloroacetate ester,trichloroacetate ester, trifluoroacetate ester (TFA-OR), methoxyacetateester, triphenylmethoxyacetate ester, phenoxyacetate ester,para-chlorophenoxyacetate ester, phenylacetate ester, diphenylacetateester (DPA-OR), nicotinate ester, 3-phenylpropionate ester, 4-pentoateester, 4-oxopentoate ester (levulinate) (Lev-OR),4,4-(ethylenedithio)pentanoate ester (LevS-OR),5-[3-bis(4-methoxyphenyl)hydroxymethoxyphenoxy]levulinate ester,pivaloate ester (Pv-OR), 1-adamantanoate ester, crotonate ester,4-methoxycrotonate ester, benzoate ester (Bz-OR), para-phenylbenzoateester, 2,4,6-trimethylbenzoate ester (mesitoate),4-(methylthiomethoxy)butyrate ester (MTMB-OR),2-(methylthiomethoxymethyl)benzoate ester (MTMT-OR),of the ester type (for example methyl carbonate, methoxymethylcarbonate, 9-fluorenylmethyl carbonate (Fmoc-OR), ethyl carbonate,2,2,2-trichloroethyl carbonate (Troc-OR),1,1-dimethyl-2,2,2-trichloroethyl carbonate (TCBOC-OR),2-(trimethylsilyl)ethyl carbonate (TMS-OR), 2-(phenylsulphonyl)ethylcarbonate (Ps-OR), 2-(triphenylphosphonio)ethyl carbonate (Peoc-OR),t-butyl carbonate (Boc-OR), isobutyl carbonate, vinyl carbonate, allylcarbonate (Alloc-OR), para-nitrophenyl carbonate, benzyl carbonate(Z-OR), para-methoxybenzyl carbonate, 3,4-dimethoxybenzyl carbonate,ortho-nitrobenzyl carbonate, para-nitrobenzyl carbonate, 2-dansylethylcarbonate (Dnseoc-OR), 2-(4-nitrophenyl)ethyl carbonate (Npeoc-OR),2-(2,4-dinitrophenyl)ethyl carbonate (Dnpeoc)), andof the sulphate type (for example allylsulphonate (Als-OR),methanesulphonate (Ms-OR), benzylsulphonate, tosylate (Ts-OR),2-[(4-nitrophenyl)ethyl]sulphonate (Npes-OR)).

Suitable catalysts for carrying out a catalytic hydrogenation in theprocess according to the invention are all customary hydrogenationcatalysts such as, for example, platinum catalysts (for example platinumplate, platinum sponge, platinum black, colloidal platinum, platinumoxide, platinum wire), palladium catalysts (for example palladiumsponge, palladium black, palladium oxide, palladium/carbon, colloidalpalladium, palladium/barium sulphate, palladium/barium carbonate,palladium hydroxide), nickel catalysts (for example reduced nickel,nickel oxide, Raney nickel), ruthenium catalysts, cobalt catalysts (forexample reduced cobalt, Raney cobalt), copper catalysts (for examplereduced copper, Raney copper, Ullmann copper). Preference is given tousing noble metal catalysts (for example platinum and palladium orruthenium catalysts), which may be applied to a suitable support (forexample carbon or silicon), rhodium catalysts (for exampletris(triphenylphosphine)rhodium(I) chloride in the presence oftriphenylphosphine). Furthermore, it is possible to use “chiralhydrogenation catalysts” (for example those comprising chiraldiphosphine ligands such as(2S,3S)-(−)-2,3-bis(diphenylphosphino)butane[(S,S)-chiraphos] or(R)-(+)-2,2′- or (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene[R(+)-BINAP or S(−)-BINAP]), whereby the proportion of an isomer in theisomer mixture is increased or the formation of another isomer isvirtually completely suppressed.

Salts of the compounds according to the invention are prepared bystandard methods. Representative acid addition salts are, for example,those formed by reaction with inorganic acids, such as, for example,sulphuric acid, hydrochloric acid, hydrobromic acid, phosphoric acid, ororganic carboxylic acids such as acetic acid, trifluoroacetic acid,citric acid, succinic acid, butyric acid, lactic acid, formic acid,fumaric acid, maleic acid, malonic acid, camphoric acid, oxalic acid,phthalic acid, propionic acid, glycolic acid, glutaric acid, stearicacid, salicylic acid, sorbic acid, tartaric acid, cinnamic acid, valericacid, picric acid, benzoic acid or organic sulphonic acids such asmethanesulphonic acid and 4-toluenesulphonic acid.

Also representative are salts of compounds according to the inventionformed from organic bases such as, for example, pyridine ortriethylamine, or those formed from inorganic bases such as, forexample, hydrides, hydroxides or carbonates of sodium, lithium, calcium,magnesium or barium, provided the compounds of the general formula (I)have a structural element suitable for this salt formation.

Synthesis methods for preparing heterocyclic N-oxides and t-amines areknown. They can be obtained using peroxy acids (for example peraceticacid and meta-chloroperbenzoic acid (MCPBA), hydrogen peroxide), alkylhydroperoxides (for example t-butyl hydroperoxide), sodium perborate anddioxiranes (for example dimethyldioxirane). These methods have beendescribed, for example, by T. L. Gilchrist, in Comprehensive OrganicSynthesis, Vol. 7, pp. 748-750, 1992, S. V. Ley, (Ed.), Pergamon Press;M. Tisler, B. Stanovnik, in Comprehensive Heterocyclic Chemistry, Vol.3, pp. 18-20, 1984, A. J. Boulton, A. McKillop, (Eds.), Pergamon Press;M. R. Grimmett, B. R. T. Keene in Advances in Heterocyclic Chemistry,Vol. 43, pp. 149-163, 1988, A. R. Katritzky, (Ed.), Academic Press; M.Tisler, B. Stanovnik, in Advances in Heterocyclic Chemistry, Vol. 9, pp.285-291, 1968, A. R. Katritzky, A. J. Boulton (Eds.), Academic Press; G.W. H. Cheeseman, E. S. G. Werstiuk in Advances in HeterocyclicChemistry, Vol. 22, pp. 390-392, 1978, A. R. Katritzky, A. J. Boulton,(Eds.), Academic Press.

EXPERIMENTAL PART Preparation Process A Preparation ofN-{2-fluoro-5-[5′-(pentafluoroethyl)-4′-(trifluoromethyl)-2′H-1,3′-bipyrazol-4-yl]benzyl}propanamide(Example Ic-1) and tert-butyl{3-[2′-methyl-5′-(pentafluoroethyl)-4′-(trifluoromethyl)-2′H-1,3′-bipyrazol-4-yl]benzyl}carbamate(Example Ic-18)

Reaction Scheme 5 shows the synthesis of the compounds (Ic-18) and(Ic-1) according to the invention.

Step 1: Synthesis of4-bromo-2′-methyl-5′-(pentafluoroethyl)-4′-(trifluoromethyl)-2′H-1,3′-bipyrazole

16.0 g (55.9 mmol) of5-fluoro-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole,8.22 g (55.9 mmol) of 4-bromo-1H-pyrazole and 15.5 g (112 mmol) ofpotassium carbonate are suspended in 250 ml of tetrahydrofuran. Thereaction mixture is heated under reflux for 16 h. The solid reactioncomponents are filtered off and washed with tetrahydrofuran. Thecombined organic phases are concentrated under reduced pressure on arotary evaporator.

This gives 23.0 g of4-bromo-2′-methyl-5′-(pentafluoroethyl)-4′-(trifluoromethyl)-2′H-1,3′-bipyrazole

¹H-NMR (400 MHz, d₆-DMSO): δ=8.58 (s, 1H); 8.16 (s, 1H); 3.32 (s, 3H);

HPLC-MS: log P^(a))=4.17

Step 2: Synthesis of tert-butyl{3-[2′-methyl-5′-(pentafluoroethyl)-4′-(trifluoromethyl)-2′H-1,3′-bipyrazol-4-yl]benzyl}carbamate(Ic-18)

500 mg (1.21 mmol) of4-bromo-2′-methyl-5′-(pentafluoroethyl)-4′-(trifluoromethyl)-2′H-1,3′-bipyrazole,304 mg (1.21 mmol) of(3-{[(tert-butoxycarbonyl)amino]methyl}phenyl)boronic acid and 69.9 mg(0.06 mmol) of tetrakis(triphenylphosphine)palladium(0) are dissolved ina mixture of 10 ml of 2-propanol and 3.69 ml of 1N sodium bicarbonatesolution. The solutions were thoroughly degassed beforehand. Under anatmosphere of protective gas, the reaction mixture is heated at 90° C.for 16 h. The reaction mixture is diluted with water and extractedrepeatedly with chloroform. The combined organic phases are dried oversodium sulphate, filtered and concentrated on a rotary evaporator underreduced pressure. The crude product is purified on an RP phase.

This gives 410 mg of tert-butyl{3-[2′-methyl-5′-(pentafluoroethyl)-4′-(trifluoromethyl)-2′H-1,3′-bipyrazol-4-yl]benzyl}carbamate(Ic-18)

¹H-NMR (400 MHz, d₆-DMSO): δ=8.68 (s, 1H); 8.44 (s, 1H); 7.64-7.19 (5H,m); 4.19 (m, 2H); 3.82 (s, 3H); 1.40 (s, 9H)

HPLC-MS: log P^(a))=4.74; mass (m/z)=540.1 [M+H]⁺.

Step 3: Synthesis of1-{3-[2′-methyl-5′-(pentafluoroethyl)-4′-(trifluoromethyl)-2′H-1,3′-bipyrazol-4-yl]phenyl}methanaminehydrochloride (1:1)

400 mg (0.74 mmol) of tert-butyl{3-[2′-methyl-5′-(pentafluoroethyl)-4′-(trifluoromethyl)-2′H-1,3′-bipyrazol-4-yl]benzyl}carbamateare dissolved in 5 ml of 4N hydrogen chloride in dioxane, and themixture is stirred for 1 h. The solvent is removed on a rotaryevaporator under reduced pressure.

This gives 410 mg of1-{3-[2′-methyl-5′-(pentafluoroethyl)-4′-(trifluoromethyl)-2′H-1,3′-bipyrazol-4-yl]phenyl}methanaminehydrochloride (1:1)

¹H-NMR (400 MHz, d₆-DMSO): δ=8.71 (s, 1H); 8.48 (s, 1H); 7.87-7.42 (m,4H)

HPLC-MS: log P^(a))=1.93, mass (m/z)=440.1 [M+H]⁺.

Step 4: Synthesis ofN-{3-[2′-methyl-5′-(pentafluoroethyl)-4′-(trifluoromethyl)-2′H-1,3′-bipyrazol-4-yl]benzyl}propanamide(Ic-1)

133 mg (0.32 mmol) of1-{3-[2′-methyl-5′-(pentafluoroethyl)-4′-(trifluoromethyl)-2′H-1,3′-bipyrazol-4-yl]phenyl}methanamineand 0.13 ml of N,N-diethyl-N-isopropylamine are dissolved in 3 ml ofchloroform, and 29 μl (0.35 mmol) of propionyl chloride are then added.After one hour, 5% strength sodium hydrogen phosphate solution is addedto the reaction mixture. The aqueous phase is extracted repeatedly withchloroform. The combined organic phases are dried over sodium sulphate,filtered and concentrated under reduced pressure on a rotary evaporator.The crude product is purified by column chromatography on silica gel.

This gives 40 mg ofN-{3-[2′-methyl-5′-(pentafluoroethyl)-4′-(trifluoromethyl)-2′H-1,3′-bipyrazol-4-yl]benzyl}propanamide(Ic-1)

¹H-NMR see NMR data in peak list

HPLC-MS: log P^(a))=3.59, mass (m/z)=496.1 [M+H]⁺.

Preparation ofN-(3-{1-[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]-1H-imidazol-4-yl}benzyl)propanamide(Ib-5) and tert-butyl(3-{1-[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]-1H-imidazol-4-yl}benzyl)carbamate(Ib-1)

Reaction Scheme 6 shows the synthesis of the compounds (Ib-5) and (Ib-1)according to the invention.

Step 1: Synthesis of5-(4-iodo-1H-imidazol-1-yl)-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole

7.0 g (24.5 mmol) of5-fluoro-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole,4.75 g (24.5 mmol) of 4-iodo-1H-imidazole and 6.76 g (48.9 mmol) ofpotassium carbonate are suspended in 100 ml of tetrahydrofuran. Thereaction mixture is heated under reflux for 16 h. The solid componentsare filtered off and washed with tetrahydrofuran. The solvent is removedunder reduced pressure on a rotary evaporator. The crude product ispurified by column chromatography on silica gel. This gives 8.73 g of5-(4-iodo-1H-imidazol-1-yl)-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole.

¹H-NMR (400 MHz, d₆-DMSO): δ=8.073 (s, 1H); 7.86 (s, 1H); 3.73 (s, 3H);

HPLC-MS: log P^(a))=3.47, mass (m/z)=460.8; 461.8 [M+H]⁺.

Step 2: Synthesis of tert-butyl(3-{1-[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]-1H-imidazol-4-yl}benzyl)carbamate(Ib-1)

2.00 g (4.35 mmol) of5-(4-iodo-1H-imidazol-1-yl)-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole,1.09 g (4.35 mmol) of(3-{[(tert-butoxycarbonyl)amino]methyl}phenyl)boronic acid and 251 mg(0.22 mmol) of tetrakis(triphenylphosphine)palladium(0) are dissolved ina mixture of 40 ml of 2-propanol and 13 ml of 1N aqueous sodiumbicarbonate solution. The solvents were thoroughly degassed beforehand.Under an atmosphere of protective gas, the reaction solution is heatedat 90° C. for 16 h. After the reaction has ended, water and chloroformare added to the reaction mixture. The organic phase is extracted withchloroform. The combined organic phases are then concentrated underreduced pressure on a rotary evaporator. The crude product is thenpurified on an RP phase. This gives 1.43 g of tert-butyl(3-{1-[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]-1H-imidazol-4-yl}benzyl)carbamate(Ib-1)

¹H-NMR (400 MHz, d₆-DMSO): δ=8.17 (s, 1H); 8.06 (s, 1H); 7.72 (s, 1H);7.65 (d, 1H); 7.55 (t, 1H); 7.45 (t, 1H); 7.25 (d, 1H); 4.17 (d, 2H);3.78 (s, 3H); 1.40 (s, 9H)

HPLC-MS: log P^(a))=4.21; mass (m/z)=540.1 [M+H]⁺.

Step 3: Synthesis of1-(3-{1-[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]-1H-imidazol-4-yl}phenyl)methanaminehydrochloride

600 mg (1.11 mmol) of tert-butyl(3-{1-[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]-1H-imidazol-4-yl}benzyl)carbamateare dissolved in 8.34 ml of 4N hydrogen chloride in dioxane, and themixture is stirred for 1 h. The solvent is removed on a rotaryevaporator under reduced pressure. This gives 650 mg of crude productwhich is used without further purification in the subsequent reactions.

HPLC-MS: log P^(a))=1.83, mass (m/z)=440.1 [M+H-HCl]⁺.

Step 4: Synthesis ofN-(3-{1-[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]-1H-imidazol-4-yl}benzyl)propanamide(Ib-5)

216 mg (0.45 mmol) of1-(3-{1-[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]-1H-imidazol-4-yl}phenyl)methanaminehydrochloride and 190 μl (1.1 mmol) of N,N-diethyl-N-isopropylamine aredissolved in chloroform, and 46 mg (0.5 mmol) of propionyl chloride arethen added. A catalytic amount of 4-(dimethylamino)pyridine is added.After one hour, 5% strength sodium hydrogen phosphate solution is addedto the reaction mixture. The aqueous phase is extracted repeatedly withchloroform. The combined organic phases are dried over sodium sulphate,filtered and concentrated under reduced pressure on a rotary evaporator.The crude product is purified by column chromatography on silica gel.

This gives 70 mg ofN-(3-{1-[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]-1H-imidazol-4-yl}benzyl)propanamide(Ib-5)

¹H-NMR see NMR data in peak list

HPLC-MS: log P^(a))=3.14, mass (m/z)=496.1 [M+H]⁺.

Preparation Process B Preparation ofN-{2-fluoro-5-[2′-methyl-5′-(pentafluoroethyl)-4′-(trifluoromethyl)-2′H-1,3′-bipyrazol-4-yl]benzyl}propanamide(Ib-8)

Reaction Scheme 7 shows the synthesis of the compound (Ib-8) accordingto the invention.

Step 1: Synthesis of2-fluoro-5-[2′-methyl-5′-(pentafluoroethyl)-4′-(trifluoromethyl)-2′H-1,3′-bipyrazol-4-yl]benzonitrile

4.00 g (10 mmol) of4-bromo-2′-methyl-5′-(pentafluoroethyl)-4′-(trifluoromethyl)-2′H-1,3′-bipyrazole,1.60 g (10 mmol) of (3-cyano-4-fluorophenyl)boronic acid and 0.56 g (0.2mmol) of tetrakis(triphenylphosphine)palladium(0) are dissolved in amixture of 80 ml of 2-propanol and 30 ml of 1N aqueous sodiumbicarbonate solution. The solvents were thoroughly degassed beforehand.Under an atmosphere of protective gas, the reaction solution is heatedat 85° C. for 5 h. After the reaction has ended, water and chloroformare added to the reaction mixture. The organic phase is extracted withchloroform. The combined organic phases are then concentrated underreduced pressure on a rotary evaporator. The crude product is thenpurified on an RP phase.

This gives 3.31 g of2-fluoro-5-[2′-methyl-5′-(pentafluoroethyl)-4′-(trifluoromethyl)-2′H-1,3′-bipyrazol-4-yl]benzonitrile.

¹H-NMR (400 MHz, d₆-DMSO): δ=8.83 (s, 1H); 8.60 (s, 1H); 8.37 (dd, 1H);8.14-8.12 (m, 1H); 7.67-7.61 (m, 1H); 3.83 (s, 3H)

HPLC-MS: log P^(a))=4.37, mass (m/z)=454.0 [M+H]⁺.

Step 2: Synthesis of1-{2-fluoro-5-[5′-(pentafluoroethyl)-4′-(trifluoromethyl)-2′H-1,3′-bipyrazol-4-yl]phenyl}methanamine

4.60 g (10 mmol) of2-fluoro-5-[2′-methyl-5′-(pentafluoroethyl)-4′-(trifluoromethyl)-2′H-1,3′-bipyrazol-4-yl]benzonitrileare dissolved in 120 ml of methanol. The solution is cooled to 0° C.,and 13 mg (0.1 mmol) of nickel(II) chloride×6H₂O are then added. Insmall portions, 768 mg (20 mmol) of sodium borohydride are added to themixture. After the last addition, the reaction mixture is slowly warmedto room temperature. After 1 h at room temperature, another 4 mg (0.03mmol) of nickel(II) chloride×6H₂O and 220 mg (5.7 mmol) pf sodiumborohydride are added to the reaction mixture. The reaction mixture isstirred at room temperature for a further hour. The reaction mixture isthen diluted with water. The mixture is extracted three times withchloroform. The combined organic phases are dried over sodium sulphate,filtered and then concentrated under reduced pressure on a rotaryevaporator. The residue is purified on an RP phase.

This gives 1.25 g of1-{2-fluoro-5-[5′-(pentafluoroethyl)-4′-(trifluoromethyl)-2′H-1,3′-bipyrazol-4-yl]phenyl}methanamine.

¹H-NMR (400 MHz, d₆-DMSO): δ=8.68 (s, 1H); 8.45 (s, 1H); 7.83 (dd, 1H);7.60-7.56 (m, 1H); 7.20 (t, 1H); 3.82 (s, 3H); 3.78 (s, 2H); 1.83 (s,2H)

HPLC-MS: log P^(a))=1.90, mass (m/z)=458.0 [M+H-HCl]⁺.

Step 3: Synthesis ofN-{2-fluoro-5-[5′-(pentafluoroethyl)-4′-(trifluoromethyl)-2′H-1,3′-bipyrazol-4-yl]benzyl}propanamide(Ib-8)

250 mg (0.55 mmol) of1-{2-fluoro-5-[5′-(pentafluoroethyl)-4′-(trifluoromethyl)-2′H-1,3′-bipyrazol-4-yl]phenyl}methanamineand 0.23 ml (1.31 mmol) of N,N-diethyl-N-isopropylamine are dissolved in3 ml of chloroform, and 52 μl (0.61 mmol) of propionyl chloride areadded. After one hour, 5% strength sodium hydrogen phosphate solution isadded to the reaction mixture. The aqueous phase is extracted repeatedlywith chloroform. The combined organic phases are dried over sodiumsulphate, filtered and concentrated under reduced pressure on a rotaryevaporator. The crude product is purified by column chromatography onsilica gel. After extraction and evaporation, the residue obtained waspurified by flash chromatography on silica gel with cyclohexane andethylacetate as eluents. This afforded 100 mg (32%) of the titlecompound.

This gives 100 mg ofN-{2-fluoro-5-[5′-(pentafluoroethyl)-4′-(trifluoromethyl)-2′H-1,3′-bipyrazol-4-yl]benzyl}propanamide(Ib-8)

¹H-NMR see NMR data in peak list

HPLC-MS: log P^(a))=3.27, mass (m/z)=514.0 [M+H]⁺.

a) Note regarding the determination of the log P values and massdetection: The determination of the given log P values was carried outin accordance with EEC Directive 79/831 Annex V.A8 by HPLC (HighPerformance Liquid Chromatography) on a reversed-phase column (C18).Agilent 1100 LC system; 50*4.6 Zorbax Eclipse Plus C18 1.8 micron;mobile phase A: acetonitrile (0.1% formic acid); mobile phase B: water(0.09% formic acid); linear gradient from 10% acetonitrile to 95%acetonitrile in 4.25 min, then 95% acetonitrile for a further 1.25 min;oven temperature 55° C.; flow rate: 2.0 ml/min. Mass detection iscarried out via an Agilend MSD system.

The stated mass is the peak of the isotope pattern of the [M+H]⁺ ion ofthe highest intensity; if the [M−H]⁻ ion was detected, the stated massis marked with².

² The stated mass is the peak of the isotope pattern of the [M−H]⁻ ionof the highest intensity.

The compounds listed in Table 1 were prepared analogously to PreparationProcesses A, B & D described above.

TABLE 1 Beisp.-Nr. Z¹ Z² Z³ R¹ R^(6a) R^(6b) A₄ A₃ A₂ A₁ M₁ M₂ Q logP^(a)) Masse ^(a)) IIc-1 C₂F₅ CF₃ CH₃ H H H C—H C—F C—H C—H H Hcyclopentyl 4.37 590.1 IIc-2 C₂F₅ CF₃ CH₃ H H H C—H C—F C—H C—H H Hpropan-2-yl 4.06 564.0 IIc-3 C₂F₅ CF₃ CH₃ H H H C—H C—F C—H C—H H Hethyl 3.85 550.1 IIc-4 C₂F₅ CF₃ CH₃ H H H C—H C—F C—H C—H H H CH₃ 3.58536.100

^(a)) Unless indicated otherwise, the following method was used todetermine the log P values and masses: The determination of the givenlog P values was carried out in accordance with EEC Directive 79/831Annex V.A8 by HPLC (High Performance Liquid Chromatography) on areversed-phase column (C18). Agilent 1100 LC system; 50*4.6 ZorbaxEclipse Plus C18 1.8 micron; mobile phase A: acetonitrile (0.1% formicacid); mobile phase B: water (0.09% formic acid); linear gradient from10% acetonitrile to 95% acetonitrile in 4.25 min, then 95% acetonitrilefor a further 1.25 min; oven temperature 55° C.; flow rate: 2.0 ml/min.Mass detection is carried out via an Agilend MSD system.

^(b)) Note for the alternative method for determining log P values andmasses: The stated log P values were determined in accordance with EECDirective 79/831 Annex V.A8 by HPLC (High Performance LiquidChromatography) using a reversed-phase column (C18). Waters ACQUITYUPLC-MS system; 2.1*50 mm Zorbax Eclipse Plus C18 1.8 μm 600 bar;injection volume: 0.5 ul about 1000 ppm; mobile phase A: acetonitrile(0.1% formic acid); mobile phase B: water (0.085% formic acid); lineargradient from 10% acetonitrile to 95% acetonitrile in 1.5 min, then 95%acetonitrile for a further 0.5 min; oven temperature 60° C.; flow rate:1.0 ml/min. Mass detection is carried out via a Waters SQD system.

The stated mass is the peak of the isotope pattern of the [M+H]⁺ ion ofthe highest intensity; if the [M−H]⁻ ion was detected, the stated massis marked with².

² The stated mass is the peak of the isotope pattern of the [M−H]⁻ ionof the highest intensity.

NMR Data of Selected Examples

The ¹H-NMR data of selected examples are stated in the form of ¹H-NMRpeak lists. For each signal peak, the δ-value in ppm and the signalintensity in brackets are listed.

Example IIc-1: ¹H-NMR(400.0 MHz, DMSO): δ = 10.267(0.6); 8.853(0.4);8.678(5.4); 8.584(0.5); 8.424(5.7); 8.415(0.6); 8.316(0.4); 7.774(1.4);7.768(1.5); 7.756(1.4); 7.750(1.3); 7.690(0.9); 7.684(0.9); 7.678(1.0);7.670(1.2); 7.663(1.0); 7.657(1.0); 7.651(0.8); 7.620(0.9); 7.605(2.0);7.590(1.0); 7.303(1.5); 7.279(1.9); 7.257(1.4); 5.756(0.5); 4.260(3.4);4.245(3.3); 3.829(1.6); 3.813(16.0); 3.537(1.1); 3.518(1.7); 3.498(1.2);3.479(0.3); 3.325(114.5); 2.675(0.6); 2.671(0.9); 2.666(0.7);2.541(0.5); 2.511(51.6); 2.506(101.6); 2.502(132.7); 2.497(96.4);2.493(46.9); 2.333(0.7); 2.329(0.9); 2.324(0.7); 1.887(1.5); 1.871(6.3);1.853(4.1); 1.836(1.8); 1.664(0.9); 1.657(1.3); 1.646(1.7); 1.628(1.3);1.614(0.4); 1.603(0.5); 1.576(0.6); 1.570(0.5); 1.564(0.5); 1.551(1.5);1.544(0.9); 1.533(1.6); 1.520(1.2); 1.513(0.7); 1.504(0.5); 1.235(1.5);1.218(1.3); 0.146(0.7); 0.008(6.7); 0.000(165.4); −0.009(6.3);−0.150(0.8) Example IIc-2: ¹H-NMR(400.0 MHz, DMSO): δ = 8.687(0.4);8.676(4.6); 8.430(0.5); 8.419(5.0); 8.315(0.5); 7.777(1.1); 7.772(1.2);7.760(1.1); 7.754(1.2); 7.689(0.7); 7.683(0.7); 7.677(0.8); 7.668(0.9);7.662(0.8); 7.656(0.8); 7.650(0.7); 7.607(0.9); 7.592(1.7); 7.577(0.8);7.302(1.3); 7.281(1.5); 7.278(1.6); 7.256(1.2); 4.256(2.9); 4.241(3.0);3.813(12.7); 3.325(147.5); 3.294(0.3); 3.201(0.4); 3.184(1.1);3.167(1.6); 3.150(1.2); 3.133(0.4); 2.676(0.5); 2.671(0.7); 2.666(0.5);2.524(2.0); 2.511(43.1); 2.507(86.0); 2.502(112.8); 2.497(81.9);2.493(39.9); 2.333(0.6); 2.329(0.8); 2.324(0.6); 1.236(16.0);1.219(15.7); 0.915(0.6); 0.146(0.6); 0.008(5.9); 0.000(145.5);−0.009(5.8); −0.150(0.6) Example IIc-3: ¹H-NMR(400.0 MHz, DMSO): δ =8.690(5.9); 8.677(0.6); 8.433(6.8); 7.775(1.4); 7.770(1.6); 7.757(1.4);7.752(1.5); 7.695(0.9); 7.689(0.8); 7.683(1.0); 7.674(1.2); 7.668(1.0);7.661(1.0); 7.656(0.9); 7.637(1.1); 7.621(2.2); 7.606(1.1); 7.308(1.7);7.286(1.9); 7.284(2.0); 7.262(1.5); 5.757(2.1); 4.235(3.9); 4.220(3.9);3.814(16.0); 3.328(77.6); 3.042(1.5); 3.024(4.8); 3.006(4.9);2.987(1.6); 2.671(0.4); 2.667(0.3); 2.524(1.3); 2.511(27.4);2.507(53.8); 2.502(69.7); 2.498(50.0); 2.333(0.3); 2.329(0.4);1.235(0.4); 1.204(5.2); 1.185(11.0); 1.167(4.9); 0.146(0.4); 0.008(3.2);0.000(81.8); −0.009(3.3); −0.150(0.4) Example IIc-4: ¹H-NMR(400.0 MHz,DMSO): δ = 8.701(3.0); 8.442(3.3); 7.765(0.7); 7.760(0.8); 7.748(0.7);7.743(0.8); 7.696(0.4); 7.690(0.4); 7.684(0.5); 7.676(0.6); 7.669(0.5);7.663(0.5); 7.657(0.4); 7.596(0.5); 7.580(1.1); 7.566(0.5); 7.312(0.8);7.290(1.0); 7.288(1.0); 7.266(0.8); 4.254(2.0); 4.238(2.0); 3.813(7.9);3.400(0.4); 3.328(164.6); 2.936(11.0); 2.675(0.5); 2.671(0.6);2.667(0.5); 2.506(79.9); 2.502(103.3); 2.497(75.0); 2.333(0.5);2.329(0.7); 2.324(0.5); 2.086(1.8); 1.398(16.0); 1.141(0.6); 1.125(0.4);0.000(0.4)

The intensity of sharp signals correlates with the height of the signalsin a printed example of an NMR spectrum in cm and shows the true ratiosof the signal intensities. In the case of broad signals, several peaksor the middle of the signal and their relative intensities may be shownin comparison to the most intense signal in the spectrum.

The lists of the ¹H NMR peaks are similar to the conventional ¹H NMRprintouts and thus usually contain all peaks listed in conventional NMRinterpretations.

In addition, like conventional ¹H NMR printouts, they may show solventsignals, signals of stereoisomers of the target compounds, whichlikewise form part of the subject matter of the invention, and/or peaksof impurities.

In the reporting of compound signals in the delta range of solventsand/or water, our lists of ¹H NMR peaks show the usual solvent peaks,for example peaks of DMSO in DMSO-d₆ and the peak of water, whichusually have a high intensity on average.

The peaks of stereoisomers of the target compounds and/or peaks ofimpurities usually have a lower intensity on average than the peaks ofthe target compounds (for example with a purity of >90%).

Such stereoisomers and/or impurities may be typical of the particularpreparation process. Their peaks can thus help in this case to identifyreproduction of our preparation process with reference to “by-productfingerprints”.

A person skilled in the art calculating the peaks of the targetcompounds by known methods (MestreC, ACD simulation, but also withempirically evaluated expected values) can, if required, isolate thepeaks of the target compounds, optionally using additional intensityfilters. This isolation would be similar to the relevant peak picking inconventional ¹H NMR interpretation.

Biological Working Examples for Applications in the Animal Health Sectorand in Crop Protection

Boophilus microplus Injection Test (BOOPMI Inj)Solvent: dimethyl sulphoxide

To produce a suitable preparation of active compound, 10 mg of activecompound are mixed with 0.5 ml of solvent, and the concentrate isdiluted with solvent to the desired concentration.

1 μl of the active compound solution is injected into the abdomen of 5engorged adult female cattle ticks (Boophilus microplus). The animalsare transferred into dishes and kept in a climate-controlled room.

The activity is assessed after 7 days by laying of fertile eggs. Eggswhose fertility is not visible from the outside are stored in aclimate-controlled cabinet until the larvae hatch after about 42 days.An efficacy of 100% means that none of the ticks has laid any fertileeggs; 0% means that all eggs are fertile.

In this test, for example, the following compounds of the PreparationExamples show an efficacy of 100% at an application rate of 20μg/animal: IIc-3, IIc-4

Ctenocephalides Felis—Oral Test (CTECFE)

Solvent: dimethyl sulphoxide

To produce a suitable preparation of active compound, 10 mg of activecompound are mixed with 0.5 ml of dimethyl sulphoxide. Dilution withcitrated cattle blood gives the desired concentration.

About 20 unfed adult cat fleas (Ctenocephalides felis) are placed into achamber which is closed at the top and bottom with gauze. A metalcylinder whose bottom end is closed with a parafilm is placed onto thechamber. The cylinder contains the blood/active ingredient preparation,which can be imbibed by the fleas through the parafilm membrane.

After 2 days, the kill in % is determined 100% means that all of thefleas have been killed; 0% means that none of the fleas have beenkilled.

In this test, for example, the following compounds of the PreparationExamples show an activity of 100% at an application rate of 100 ppm:IIc-4

In this test, for example, the following compounds of the PreparationExamples show an activity of 95% at an application rate of 100 ppm:IIc-3

Lucilia cuprina Test (LUCICU)Solvent: dimethyl sulphoxide

To produce a suitable preparation of active compound, 10 mg of activecompound are mixed with 0.5 ml of dimethyl sulphoxide, and theconcentrate is diluted with water to the desired concentration.

About 20 L1 larvae of the Australian sheep blowfly (Lucilia cuprina) aretransferred into a test vessel containing minced horsemeat and theactive compound preparation of the desired concentration.

After 2 days, the kill in % is determined 100% means that all of thelarvae have been killed; 0% means that none of the larvae have beenkilled.

In this test, for example, the following compounds of the PreparationExamples show an activity of 100% at an application rate of 100 ppm:IIc-3, IIc-4

Musca domestica Test (MUSCDO)Solvents: dimethyl sulphoxide

To produce a suitable preparation of active compound, 10 mg of activecompound are mixed with 0.5 ml of dimethyl sulphoxide, and theconcentrate is diluted with water to the desired concentration.

Vessels containing a sponge treated with sugar solution and the activecompound preparation of the desired concentration are populated with 10adult houseflies (Musca domestica).

After 2 days, the kill in % is determined 100% means that all of theflies have been killed; 0% means that none of the flies have beenkilled.

In this test, for example, the following compounds of the PreparationExamples show an activity of 100% at an application rate of 100 ppm:IIc-4

Meloidogyne incognita Test (MELGIN)Solvent: 125.0 parts by weight of acetone

To prepare a suitable active compound preparation, 1 part by weight ofactive compound is mixed with the stated amount of solvent and theconcentrate is diluted with water to the desired concentration.

Vessels are filled with sand, active compound solution, an egg/larvaesuspension of the southern root-knot nematode (Meloidogyne incognita)and lettuce seeds. The lettuce seeds germinate and the plants develop.On the roots, galls are formed.

After 14 days, the nematicidal efficacy in % is determined by theformation of galls. 100% means that no galls have been found; 0% meansthat the number of galls on the treated plants corresponds to theuntreated control.

In this test, for example, the following compounds of the PreparationExamples show an activity of 90% at an application rate of 20 ppm:IIc-3, IIc-4

Myzus persicae—Spray Test (MYZUPE)Solvents: 78 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide        Emulsifier: alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is dissolved using the stated parts by weight ofsolvent and made up with water comprising an emulsifier concentration of1000 ppm until the desired concentration is reached. To produce furthertest concentrations, the preparation is diluted withemulsifier-containing water.

Discs of Chinese cabbage leaves (Brassica pekinensis) infested by allstages of the green peach aphid (Myzus persicae) are sprayed with anactive compound preparation of the desired concentration.

After 6 days, the efficacy in % is determined. 100% here means that allof the aphids have been killed; 0% means that no aphids have beenkilled.

In this test, for example, the following compounds of the PreparationExamples show an activity of 90% at an application rate of 100 g/IIc-3

Phaedon cochleariae—Spray Test (PHAECO)Solvents: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide        Emulsifier: alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is dissolved using the stated parts by weight ofsolvent and made up with water comprising an emulsifier concentration of1000 ppm until the desired concentration is reached. To produce furthertest concentrations, the preparation is diluted withemulsifier-containing water.

Discs of Chinese cabbage leaves (Brassica pekinensis) are sprayed withan active compound preparation of the desired concentration and, afterdrying, populated with larvae of the mustard beetle (Phaedoncochleariae).

After 7 days, the efficacy in % is determined. 100% means that all ofthe beetle larvae have been killed; 0% means that none of the beetlelarvae have been killed.

In this test, for example, the following compounds of the PreparationExamples show an efficacy of 100% at an application rate of 100 g/ha:IIc-1, IIc-2, IIc-3, IIc-4

Tetranychus urticae—Spray Test, OP-Resistant (TETRUR)Solvents: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide        Emulsifier: alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is dissolved using the stated parts by weight ofsolvent and made up with water comprising an emulsifier concentration of1000 ppm until the desired concentration is reached. To produce furthertest concentrations, the preparation is diluted withemulsifier-containing water.

Discs of bean leaves (Phaseolus vulgaris) which are infested by allstages of the greenhouse red spider mite (Tetranychus urticae) aresprayed with an active compound preparation of the desiredconcentration.

After 6 days, the efficacy in % is determined. 100% means that all ofthe spider mites have been killed; 0% means that none of the spidermites have been killed.

In this test, for example, the following compounds of the PreparationExamples show an activity of 100% at an application rate of 100 g/ha:IIc-2, IIc-3, IIc-4

In this test, for example, the following compounds of the PreparationExamples show an activity of 90% at an application rate of 100 g/ha:IIc-1

We claim:
 1. Compounds of the general formula (II)

in which R¹ represents hydrogen, optionally substituted C₁-C₆-alkyl,C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₃-C₇-cycloalkyl, C₁-C₆-alkylcarbonyl,C₁-C₆-alkoxycarbonyl, aryl-(C₁-C₃)-alkyl, heteroaryl-(C₁-C₃)-alkyl, M¹and M² each independently of one another represent hydrogen, cyano orrepresent optionally mono- or polysubstituted C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxycarbonyl, orM¹ and M² with the carbon atom to which they are attached form anoptionally substituted 3-, 4-, 5- or 6-membered ring which optionallycontains 0, 1 or 2 nitrogen atoms and/or 0, 1 or 2 oxygen atoms and/or0, 1 or 2 sulphur atoms, the chemical groupings A₁ represents CR² ornitrogen, A₂ represents CR³ or nitrogen, A₃ represents CR⁴ or nitrogenand A₄ represents CR⁵ or nitrogen, but where not more than three of thechemical groupings A₁ to A₄ simultaneously represent nitrogen; R², R³,R⁴ and R⁵ independently of one another represent hydrogen, halogen,cyano, nitro, optionally substituted C₁-C₆-alkyl, C₃-C₆-cycloalkyl,C₁-C₆-alkoxy, N—C₁-C₆-alkoxy-imino-C₁-C₃-alkyl, C₁-C₆-alkylsulphanyl,C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, N—C₁-C₆-alkylamino orN,N-di-C₁-C₆-alkylamino; if none of the groupings A₂ and A₃ representsnitrogen, R³ and R⁴ together with the carbon atom to which they areattached may form a 5- or 6-membered ring which contains 0, 1 or 2nitrogen atoms and/or 0 or 1 oxygen atom and/or 0 or 1 sulphur atom, orif none of the groupings A₁ and A₂ represents nitrogen, R² and R³together with the carbon atom to which they are attached may form a6-membered ring which contains 0, 1 or 2 nitrogen atoms; W representsoxygen or sulphur; Q represents hydrogen, hydroxy, amino or one of theoptionally substituted groupings alkyl, alkoxy, alkenyl, alkynyl,cycloalkyl, heterocycloalkyl, cycloalkylalkyl, arylalkyl,heteroarylalkyl or represents a grouping N-alkylamino,N-alkylcarbonylamino, N,N-dialkylamino; or Q represents an unsaturated6-membered carbocycle which is optionally mono- or polysubstituted by Vor an unsaturated 5- or 6-membered heterocyclic ring which is optionallymono- or polysubstituted by V, where V independently of one anotherrepresent halogen, cyano, nitro, optionally substituted alkyl, alkenyl,alkynyl, cycloalkyl, alkoxy, N-alkoxyiminoalkyl, alkylsulphanyl,alkylsulphinyl, alkylsulphonyl, N,N-dialkylamino, T represents one ofthe 5-membered heteroaromatics T1-T8 listed below, where the bond to thepyrazole head group is marked with an asterisk,

where R⁶ independently of one another represent halogen, cyano, nitro,amino or optionally substituted C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₆-alkylcarbonyl, C₁-C₆-alkylsulphanyl, C₁-C₆-alkylsulphinyl,C₁-C₆-alkylsulphonyl, and n represents the values 0-2; Z¹ representsoptionally substituted alkyl and cycloalkyl, and Z² represents hydrogen,halogen, cyano, nitro, amino or optionally substituted alkyl,alkylcarbonyl, alkylsulphanyl, alkylsulphinyl, alkylsulphonyl, and Z³represents hydrogen or optionally substituted alkyl, cycloalkyl,alkenyl, alkynyl, aryl or hetaryl.
 2. Compounds according to claim 1 inwhich R¹ represents hydrogen, optionally substituted C₁-C₆-alkyl,C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₃-C₇-cycloalkyl, C₁-C₆-alkylcarbonyl,C₁-C₆-alkoxycarbonyl, aryl-(C₁-C₃)-alkyl, heteroaryl-(C₁-C₃)-alkyl, M¹and M² each independently of one another represent hydrogen, cyano orrepresent optionally mono- or polysubstituted C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxycarbonyl, orM¹ and M² with the carbon atom to which they are attached form anoptionally substituted 3-, 4-, 5- or 6-membered ring which optionallycontains 0, 1 or 2 nitrogen atoms and/or 0, 1 or 2 oxygen atoms and/or0, 1 or 2 sulphur atoms, the chemical groupings A₁ represents CR² ornitrogen, A₂ represents CR³ or nitrogen, A₃ represents CR⁴ or nitrogenand A₄ represents CR⁵ or nitrogen, but where not more than three of thechemical groupings A₁ to A₄ simultaneously represent nitrogen; R², R³,R⁴ and R⁵ independently of one another represent hydrogen, halogen,cyano, nitro, optionally substituted C₁-C₆-alkyl, C₃-C₆-cycloalkyl,C₁-C₆-alkoxy, N—C₁-C₆-alkoxyimino-C₁-C₃-alkyl, C₁-C₆-alkylsulphanyl,C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, N—C₁-C₆-alkylamino orN,N-di-C₁-C₆-alkylamino; if none of the groupings A₂ and A₃ representsnitrogen, R³ and R⁴ together with the carbon atom to which they areattached may form a 5- or 6-membered ring which contains 0, 1 or 2nitrogen atoms and/or 0 or 1 oxygen atom and/or 0 or 1 sulphur atom, orif none of the groupings A₁ and A₂ represents nitrogen, R² and R³together with the carbon atom to which they are attached may form a6-membered ring which contains 0, 1 or 2 nitrogen atoms; W representsoxygen or sulphur; Q represents hydrogen, formyl, hydroxy, amino or oneof the optionally substituted groupings C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₂-C₇-heterocycloalkyl, C₁-C₄-alkoxy,C₃-C₆-cycloalkyl-C₁-C₆-alkyl, aryl-(C₁-C₃)-alkyl,heteroaryl-(C₁-C₃)-alkyl or represents a grouping N—C₁-C₄-alkylamino,N—C₁-C₄-alkylcarbonylamino, N,N-di-C₁-C₄-alkylamino; or Q represents anunsaturated 6-membered carbocycle which is optionally mono- orpolysubstituted by V or an unsaturated 5- or 6-membered heterocyclicring which is optionally mono- or polysubstituted by V, where Vindependently of one another represent halogen, cyano, nitro, optionallysubstituted C₁-C₆-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl,C₁-C₆-alkoxy, N—C₁-C₆-alkoxy-imino-C₁-C₃-alkyl, C₁-C₆-alkylsulphanyl,C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, N,N-di-(C₁-C₆-alkyl)amino; Trepresents one of the 5-membered heteroaromatics T1-T8 listed below,where the bond to the pyrazole head group is marked with an asterisk,

where R⁶ independently of one another represent halogen, cyano, nitro,amino or optionally halogen-substituted C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₆-alkylcarbonyl, C₁-C₆-alkylsulphanyl, C₁-C₆-alkylsulphinyl,C₁-C₆-alkylsulphonyl, and n represents the values 0-1; Z¹ representsoptionally substituted C₁-C₆-haloalkyl, C₃-C₆-halocycloalkyl, and Z²represents hydrogen, halogen, cyano, nitro, amino or optionallysubstituted C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkylsulphanyl,C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, and Z³ represents hydrogenor optionally substituted C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-alkenyl,C₃-C₆-alkynyl, aryl or hetaryl.
 3. Compounds according to claim 1 inwhich R¹ represents hydrogen or represents C₁-C₆-alkyl, C₃-C₆-alkenyl,C₃-C₆-alkynyl, C₃-C₇-cycloalkyl, C₁-C₆-alkylcarbonyl,C₁-C₆-alkoxycarbonyl, aryl-(C₁-C₃)-alkyl, heteroaryl-(C₁-C₃)-alkyl whichare optionally mono- to heptasubstituted independently of one another byfluorine, chlorine, cyano, C₁-C₆-alkoxy and C₁-C₆-alkoxycarbonyl, M¹represents hydrogen, M² represents hydrogen, cyano or representsC₁-C₆-alkyl, C₂-C₆-alkenyl, C₃-C₆-cycloalkyl, C₁-C₃-alkoxycarbonyl whichare optionally mono- to pentasubstituted independently of one another byfluorine, chlorine, cyano or C₁-C₃-alkoxy, M¹ and M² with the carbonatom to which they are attached form an optionally substituted3-membered ring, the chemical groupings A₁ represents CR² or nitrogen,A₂ represents CR³ or nitrogen, A₃ represents CR⁴ or nitrogen and A₄represents CR⁵ or nitrogen, but where not more than three of thechemical groupings A₁ to A₄ simultaneously represent nitrogen; R², R³,R⁴ and R⁵ independently of one another represent hydrogen, fluorine,chlorine, bromine, iodine, cyano, nitro or represent C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, N—C₁-C₆-alkoxyimino-C₁-C₃-alkyl,C₁-C₆-alkylsulphanyl, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl,N—C₁-C₆-alkylamino or N,N-di-C₁-C₆-alkylamino which are optionally mono-to pentasubstituted independently of one another by fluorine, chlorine,cyano, hydroxycarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyl orphenyl; W represents oxygen or sulphur; Q represents hydrogen, amino orone of the groupings C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₃-C₆-cycloalkyl, C₂-C₅-heterocycloalkyl, C₁-C₄-alkoxy,C₃-C₆-cycloalkyl-C₁-C₆-alkyl, aryl-(C₁-C₃)-alkyl,heteroaryl-(C₁-C₃)-alkyl, N—C₁-C₄-alkylamino, N—C₁-C₄-alkylcarbonylaminoor N,N-di-C₁-C₄-alkylamino which are optionally independently of oneanother mono- to pentasubstituted by hydroxy, nitro, amino, fluorine,chlorine, C₁-C₆-alkyl, C₁-C₆-alkoxy, cyano, hydroxycarbonyl,C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbamoyl, C₃-C₇-cycloalkylcarbamoyl,phenyl; or Q represents aryl substituted by 0-4 substituents V or a 5-or 6-membered heteroaromatic substituted by 0-4 substituents V, where Vindependently of one another represent halogen, cyano, nitro, optionallysubstituted C₁-C₆-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl,C₁-C₆-alkoxy, N—C₁-C₆-alkoxyimino-C₁-C₃-alkyl, C₁-C₆-alkylsulphanyl,C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, N,N-di-(C₁-C₆-alkyl)amino; Trepresents one of the 5-membered heteroaromatics T1-T8 listed below,where the bond to the pyrazole head group is marked with an asterisk,

where R⁶ independently of one another represent fluorine, chlorine,bromine, iodine, cyano, nitro, amino or represents C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₆-alkylcarbonyl, C₁-C₆-alkylsulphanyl,C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl which are optionallyindependently of one another mono to pentasubstituted by fluorine and/orchlorine, and n represents the values 0-1; Z¹ represents optionallysubstituted C₁-C₆-haloalkyl, C₃-C₆-halocycloalkyl, and Z² representshydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, amino orrepresents C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkylsulphanyl,C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl which are optionallyindependently of one another mono- to pentasubstituted by fluorineand/or chlorine, and Z³ represents hydrogen or optionally substitutedC₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₄-alkenyl, C₃-C₄-alkynyl, aryl orhetaryl.
 4. Compounds according to claim 1 in which R¹ representshydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl,s-butyl, t-butyl, methoxymethyl, ethoxymethyl, propoxymethyl,methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl,n-butylcarbonyl, isobutylcarbonyl, s-butylcarbonyl, t-butylcarbonyl,methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl,n-butoxycarbonyl, isobutoxycarbonyl, s-butoxycarbonyl, t-butoxycarbonyl,cyanomethyl, 2-cyanoethyl, benzyl, 4-methoxybenzyl, pyrid-2-ylmethyl,pyrid-3-ylmethyl, pyrid-4-ylmethyl, 6-chloropyrid-3-ylmethyl; M¹represents hydrogen, M² represents hydrogen, methyl, ethyl,difluoromethyl, trichloromethyl, dichlorofluoromethyl, trifluoromethyl,cyclopropyl, cyclobutyl, methoxycarbonyl, ethoxycarbonyl, M¹ and M² withthe carbon atom to which they are attached form a 3-membered carbocycle,the chemical groupings A₁ represents CR² or nitrogen, A₂ represents CR³or nitrogen, A₃ represents CR⁴ or nitrogen and A₄ represents CR⁵ ornitrogen, but where not more than three of the chemical groupings A₁ toA₄ simultaneously represent nitrogen; R² and R⁵ independently of oneanother represent hydrogen, methyl, fluorine or chlorine and R³ and R⁴independently of one another represent hydrogen, fluorine, chlorine,bromine, iodine, cyano, nitro, methyl, ethyl, fluoromethyl,difluoromethyl, chlorodifluoromethyl, trifluoromethyl,2,2,2-trifluoroethyl, methoxy, ethoxy, n-propoxy, 1-methylethoxy,fluoromethoxy, difluoromethoxy, chlorodifluoromethoxy,dichlorofluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy,2-chloro-2,2-difluoroethoxy, pentafluoroethoxy, N-methoxyiminomethyl,1-(N-methoxyimino)ethyl, methylsulfanyl, trifluoromethylsulphanyl,methylsulphonyl, methylsulphinyl, trifluoromethylsulphonyl,trifluoromethylsulphinyl; W represents oxygen or sulphur; Q representshydrogen, methyl, ethyl, n-propyl, isopropyl, t-butyl, 1-methylpropyl,n-butyl, 2-methylpropyl, 2-methylbutyl, hydroxymethyl, 2-hydroxyethyl,2-hydroxypropyl, cyanomethyl, 2-cyanoethyl, trifluoromethyl,1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,1-trifluoromethylethyl, 2,2-difluoropropyl, 3,3,3-trifluoropropyl,2,2-dimethyl-3-fluoropropyl, cyclopropyl, 1-cyanocyclopropyl,cyclopropylmethyl, cyclobutyl, cyclopentyl, cyclohexyl,1-cyclopropylethyl, bis(cyclopropyl)methyl,2,2-dimethylcyclopropylmethyl, 2-phenylcyclopropyl,2,2-dichlorocyclopropyl, trans-2-chlorocyclopropyl,cis-2-chlorocyclopropyl, 2,2-difluorocyclopropyl,trans-2-fluorocyclopropyl, cis-2-fluorocyclopropyl,trans-4-hydroxycyclohexyl, 4-trifluoromethylcyclohexyl, ethenyl,1-methylethenyl, prop-1-enyl, 2-methylprop-1-enyl, 3-methylbut-1-enyl,3,3,3-trifluoroprop-1-enyl, 1-ethylethenyl, 1-methylprop-1-enyl,prop-2-ynyl, 3-fluoroprop-2-enyl, oxetan-3-yl, thietan-3-yl,1-oxidothietan-3-yl, 1,1-dioxidothietan-3-yl, tetrahydrofuran-3-yl,1,1-dioxidotetrahydrothiophen-3-yl, isoxazol-3-ylmethyl,1,2,4-triazol-3-ylmethyl, 3-methyloxetan-3-ylmethyl, benzyl,2,6-difluorophenylmethyl, 3-fluorophenylmethyl, 2-fluorophenylmethyl,2,5-difluorophenylmethyl, 1-phenylethyl, 4-chlorophenylethyl,2-trifluoromethylphenylethyl, 1-pyridin-2-ylethyl, pyridin-2-ylmethyl,5-fluoropyridin-2-ylmethyl, (6-chloropyridin-3-yl)methyl,pyrimidin-2-ylmethyl, thiophen-2-yl-methyl, 2-ethoxyethyl,2-methoxyethyl, 1-(methylsulphanyl)ethyl, 2-(methylsulphanyl)ethyl,1-methyl-2-(ethylsulphanyl)ethyl,2-methyl-1-(methylsulphanyl)propan-2-yl, methoxycarbonyl,ethoxycarbonyl, methoxycarbonylmethyl, NH₂, N-ethylamino, N-allylamino,N,N-dimethylamino, N,N-diethylamino, methoxy, ethoxy, propoxy,isopropoxy, tert-butoxy; or Q represents phenyl, naphthyl, pyridazine,pyrazine, pyrimidine, triazine, pyridine, pyrazole, thiazole,isothiazole, oxazole, isoxazole, triazole, imidazole, furan, thiophene,pyrrole, oxadiazole, thiadiazole substituted by 0, 1, 2 or 3substituents V, where V independently of one another represent fluorine,chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, difluoromethyl,trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl,trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl,2,2,2-trifluoroethyl, 1,2,2,2-tetrafluoroethyl,1-chloro-1,2,2,2-tetrafluoroethyl, 2,2,2-trichloroethyl,2-chloro-2,2-difluoroethyl, 1,1-difluoroethyl, pentafluoroethyl,heptafluoro-n-propyl, heptafluoroisopropyl, nonafluoro-n-butyl,cyclopropyl, cyclobutyl, methoxy, ethoxy, n-propoxy, 1-methylethoxy,fluoromethoxy, difluoromethoxy, chlorodifluoromethoxy,dichlorofluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy,2-chloro-2,2-difluoroethoxy, pentafluoroethoxy, N-methoxyiminomethyl,1-(N-methoxyimino)ethyl, methylsulphanyl, methylsulphonyl,methylsulphinyl, trifluoromethylsulphonyl, trifluoromethylsulphinyl,trifluoromethylsulphanyl, N,N-dimethylamino; T represents one of the5-membered heteroaromatics T1-T8 listed below, where the bond to thepyrazole head group is marked with an asterisk,

where R⁶ independently of one another represent fluorine, chlorine,cyano, nitro, amino, methyl, ethyl, propyl, 1-methylethyl, tert-butyl,trifluoromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy,2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, methylcarbonyl,ethylcarbonyl, trifluoromethylcarbonyl, methylsulphanyl,methylsulphinyl, methylsulphonyl, trifluoromethylsulphonyl,trifluoromethylsulphanyl, trifluoromethylsulphinyl, and n represents thevalues 0-1; Z¹ represents difluoromethyl, trichloromethyl,chlorodifluoromethyl, dichlorofluoromethyl, trifluoromethyl,bromodichloromethyl, 1-fluoroethyl, 1-fluoro-1-methylethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,1,2,2,2-tetrafluoroethyl, 1-chloro-1,2,2,2-tetrafluoroethyl,2,2,2-trichloroethyl, 2-chloro-2,2-difluoroethyl, 1,1-difluoroethyl,pentafluoroethyl, heptafluoro-n-propyl, heptafluoroisopropyl,nonafluoro-n-butyl, cyclopropyl, 1-chlorocyclopropyl,1-fluorocyclopropyl, 1-bromocyclopropyl, 1-cyanocyclopropyl,1-trifluoromethylcyclopropyl, cyclobutyl or2,2-difluoro-1-methylcyclopropyl, and Z² represents hydrogen, fluorine,chlorine, bromine, iodine, cyano, nitro, amino, methyl, ethyl,1,14-butyl, difluoromethyl, trichloromethyl, chlorodifluoromethyl,dichlorofluoromethyl, trifluoromethyl, bromodichloromethyl,1-fluoroethyl, 1-fluoro-1-methylethyl, 2-fluoroethyl, 2,2-difluoroethyl,2,2,2-trifluoroethyl, 1,2,2,2-tetrafluoroethyl,1-chloro-1,2,2,2-tetrafluoroethyl, 2,2,2-trichloroethyl,2-chloro-2,2-difluoroethyl, 1,1-difluoroethyl, pentafluoroethyl,heptafluoro-n-propyl, heptafluoroisopropyl, nonafluoro-n-butyl,methylsulphanyl, methylsulphinyl, methylsulphonyl, ethylthio,ethylsulphinyl, ethylsulphonyl, trifluoromethylsulphanyl,trifluoromethylsulphinyl, trifluoromethylsulphonyl,chlorodifluoromethylsulphanyl, chlorodifluoromethylsulphinyl,chlorodifluoromethylsulphonyl, dichlorofluoromethylsulphanyl,dichlorofluoromethylsulphinyl, dichlorofluoromethylsulphonyl and Z³represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl,isobutyl, s-butyl, t-butyl, 1-propenyl, 1-propynyl, 1-butynyl,difluoromethyl, trichloromethyl, chlorodifluoromethyl,dichlorofluoromethyl, trifluoromethyl, 1-fluoroethyl,1-fluoro-1-methylethyl, 2-fluoroethyl, 2,2-difluoroethyl,2,2,2-trifluoroethyl, phenyl, 2-chlorophenyl, 3-chlorophenyl,4-chlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl,3,4-dichlorophenyl, 2,6-dichlorophenyl,2,6-dichloro-4-trifluoromethylphenyl,3-chloro-5-trifluoromethylpyridin-2-yl.
 5. Compounds according to claim1 in which Z¹ represents trifluoromethyl, 1-chlorocyclopropyl,1-fluorocyclopropyl or pentafluoroethyl, Z² represents trifluoromethyl,nitro, methylsulphanyl, methylsulphinyl, methylsulphonyl, fluorine,chlorine, bromine, cyano or iodine, Z³ represents methyl, ethyl,n-propyl or hydrogen, R¹ represents hydrogen, methyl, ethyl, n-propyl,isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, methoxymethyl,ethoxymethyl, propoxymethyl, methylcarbonyl, ethylcarbonyl,n-propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, isobutylcarbonyl,s-butylcarbonyl, t-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl,n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl,isobutoxycarbonyl, s-butoxycarbonyl, t-butoxycarbonyl, cyanomethyl,2-cyanoethyl, benzyl, 4-methoxybenzyl, pyrid-2-ylmethyl,pyrid-3-ylmethyl, pyrid-4-ylmethyl, 6-chloropyrid-3-ylmethyl; M¹represents hydrogen; M² represents hydrogen or methyl; M¹ and M² withthe carbon atom to which they are attached form a 3-membered carbocycle,A¹ and A⁴ represent CH, A² represents CH or N, A₃ represents CR⁴ and R⁴represents methyl, ethyl, fluorine, chlorine, bromine or iodine, Trepresents one of the 5-membered heteroaromatics T1-T8 listed below,where the bond to the pyrazole head group is marked with an asterisk,

where R⁶ represents hydrogen, methyl, ethyl, 2-methylethyl,2,2-dimethylethyl, fluorine, chlorine, bromine, iodine, nitro,trifluoromethyl, amino, W represents oxygen and Q represents hydrogen,methyl, ethyl, n-propyl, 1-methylethyl, 1,1-dimethylethyl, n-butyl,1-methylpropyl, 2-methylpropyl, 2-methylbutyl, hydroxymethyl,2-hydroxypropyl, cyanomethyl, 2-cyanoethyl, 2-fluoroethyl,2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1-trifluoromethylethyl,2,2-difluoropropyl, 3,3,3-trifluoropropyl, 2,2-dimethyl-3-fluoropropyl,cyclopropyl, cyclopropylmethyl, cyclobutyl, cyclopentyl, cyclohexyl,1-cyclopropylethyl, bis(cyclopropyl)methyl,2,2-dimethylcyclopropylmethyl, 2-phenylcyclopropyl,2,2-dichlorocyclopropyl, trans-2-chlorocyclopropyl,cis-2-chlorocyclopropyl, 2,2-difluorocyclopropyl,trans-2-fluorocyclopropyl, cis-2-fluorocyclopropyl,trans-4-hydroxycyclohexyl, 4-trifluoromethylcyclohexyl, ethenyl,1-methylethenyl, prop-1-enyl, 2-methylprop-1-enyl, 3-methylbut-1-enyl,3,3,3-trifluoroprop-1-enyl, 1-ethylethenyl, 1-methylprop-1-enyl,prop-2-ynyl, 3-fluoroprop-2-enyl, oxetan-3-yl, thietan-3-yl,1-oxidothietan-3-yl, 1,1-dioxidothietan-3-yl, isoxazol-3-ylmethyl,1,2,4-triazol-3-ylmethyl, 3-methyloxetan-3-ylmethyl, benzyl,2,6-difluorophenylmethyl, 3-fluorophenylmethyl, 2-fluorophenylmethyl,2,5-difluorophenylmethyl, 1-phenylethyl, 4-chlorophenylethyl,2-trifluormethylphenylethyl, 1-pyridin-2-ylethyl, pyridin-2-ylmethyl,(6-chloropyridin-3-yl)methyl, 5-fluoropyridin-2-ylmethyl,pyrimidin-2-ylmethyl, methoxy, 2-ethoxyethyl, 2-(methylsulphanyl)ethyl,1-methyl-2-(ethylsulphanyl)ethyl,2-methyl-1-(methylsulphanyl)propan-2-yl, methoxycarbonyl,methoxycarbonylmethyl, NH₂, N-ethylamino, N-allylamino,N,N-dimethylamino, N,N-diethylamino, methoxy, ethoxy, propoxy,isopropoxy, tert-butoxy; or Q represents phenyl, naphthyl, pyridazine,pyrazine, pyrimidine, triazine, pyridine, pyrazole, thiazole,isothiazole, oxazole, isoxazole, triazole, imidazole, furan, thiophene,pyrrole, oxadiazole, thiadiazole substituted by 0, 1, 2 or 3substituents V, where V independently of one another represent fluorine,chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, difluoromethyl,trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl,trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl,2,2,2-trifluoroethyl, 1,2,2,2-tetrafluoroethyl,1-chloro-1,2,2,2-tetrafluoroethyl, 2,2,2-trichloroethyl,2-chloro-2,2-difluoroethyl, 1,1-difluoroethyl, pentafluoroethyl,heptafluoro-n-propyl, heptafluoroisopropyl, nonafluoro-n-butyl,cyclopropyl, cyclobutyl, methoxy, ethoxy, n-propoxy, 1-methylethoxy,fluoromethoxy, difluoromethoxy, chlorodifluoromethoxy,dichlorofluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy,2-chloro-2,2-difluoroethoxy, pentafluoroethoxy, N-methoxyiminomethyl,1-(N-methoxyimino)ethyl, methylsulphanyl, methylsulphonyl,methylsulphinyl, trifluoromethylsulphonyl, trifluoromethylsulphinyl,trifluoromethylsulphanyl, N,N-dimethylamino.
 6. Compounds of the generalformulae (IIa), (IIb), (IIc), (IId), (IIe), (IIf), (IIg), (IIh) in whichthe radicals A₁-A₄, n, W, Q, R¹, R⁶, M¹, M² and Z¹-Z³ may assume themeanings according to claim
 1.


7. Use of compounds of the general formula (II) or the general formulae(IIa) to (IIh) according to claim 1 for controlling insects, arachnidsand nematodes.
 8. Pharmaceutical compositions comprising at least onecompound according to claim
 1. 9. Compounds according to claim 1 for useas medicaments.
 10. Use of compounds according to claim 1 for preparingpharmaceutical compositions for controlling parasites on animals. 11.Process for preparing crop protection compositions comprising compoundsaccording to claim 1 and customary extenders and/or surfactants. 12.Method for controlling pests, characterized in that a compound accordingto claim 1 is allowed to act on the pests and/or their habitat.
 13. Useof compounds according to claim 1 for protecting the propagationmaterial of plants.